EP1718302A1 - Organic compounds - Google Patents
Organic compoundsInfo
- Publication number
- EP1718302A1 EP1718302A1 EP05712759A EP05712759A EP1718302A1 EP 1718302 A1 EP1718302 A1 EP 1718302A1 EP 05712759 A EP05712759 A EP 05712759A EP 05712759 A EP05712759 A EP 05712759A EP 1718302 A1 EP1718302 A1 EP 1718302A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- lower alkyl
- hydrogen
- compound
- treatment
- halogen
- 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.)
- Withdrawn
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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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
Definitions
- the present invention relates to the use of certain imidazolylalkyl-pyridines in the treatment of ocular disorders. More particularly, the present invention relates to the use of compounds of formula I,
- Rj. is hydrogen, lower alkyl, halogen with an atomic number of 9 to 35 or amino optionally mono- or disubstituted by lower alkyl
- R 2 . and R 3 . independently of one another are hydrogen or lower alkyl
- R 4 . is hydrogen, hydroxy, lower alkyl, lower alkoxy or halogen with an atomic number of 9 to 35, in free base or acid addition salt form
- the bridge between the pyridine and the imidazole, illustrated as methylene is methylene or ethylene.
- Rj. is hydrogen, lower alkyl, halogen with an atomic number of 9 to 35 or amino optionally mono- or disubstituted by lower alkyl
- R 2 . and R 3 . independently of one another are hydrogen or lower alkyl
- R 4 . is hydrogen, hydroxy, lower alkyl, lower alkoxy or halogen with an atomic number of 9 to 35
- the bridge between the pyridine and the imidazole, illustrated as methylene is methylene or ethylene.
- a second aspect of the invention provides a use of a compound of formula (I) in the manufacture of a medicament for the treatment of ocular neovascularization, said compound of formula (I) being
- Rj. is hydrogen, lower alkyl, halogen with an atomic number of 9 to 35 or amino optionally mono- or disubstituted by lower alkyl
- R 2 . and R 3 . independently of one another are hydrogen or lower alkyl
- ⁇ . is hydrogen, hydroxy, lower alkyl, lower alkoxy or halogen with an atomic number of 9 to 35
- Figure 1 illustrates the effect of a compound of the present invention on capillary network formation in cultured human umbilical vein endothelial cells (HUVECs).
- alkyl and alkoxy groups denote a radical having up to 7 carbon atoms, preferably up to 4 carbon atoms and more preferably up to 2 carbon atoms. Consequently, lower alkyl has especially up to 7 carbon atoms, preferably up to 4 carbon atoms, and in particular up to 2 carbon atoms and is, for example, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, or hexyl.
- lower alkoxy has up to 7 carbon atoms, preferably up to 4 carbon atoms, and in particular up to 2 carbon atoms and is, for example, methoxy, ethoxy, propoxy, butoxy, tert-butoxy or hexyloxy.
- these preferably have one or two carbon atoms and especially signify methyl or methoxy.
- the imidazolylmethyl radical is preferably in position 2 of the pyridine.
- Rj is preferably methyl or ethyl, more preferably methyl.
- R and R 3 are preferably each hydrogen.
- R is preferably methyl, ethyl or hydrogen, more preferably methyl or hydrogen, and in particular hydrogen.
- the compound A of Example 1 is strongly preferred.
- Rj is lower alkyl
- R 2 and R 3 independently of one another are hydrogen or lower alkyl
- t is hydrogen, lower alkyl or halogen with an atomic number of 9 to 35.
- Ri is methyl
- R 2 and R 3 independently of one another are hydrogen or methyl
- R) is hydrogen, methyl or halogen with an atomic number of 9 to 35.
- Halogen with an atomic number of 9 to 35 denote in particular a fluorine and chlorine residue, more particularly a chlorine residue.
- the compounds of formula (I) may be present in free base form or in the form of their acid addition salts, including, for example, hydrogen fumarate and fumarate salt forms. Acid addition salts may be produced from the free bases in known manner, and vice versa.
- the compounds of formula (I) are known, e.g., from US 5,856,343 and US 5,635,521, which are incorporated herein by reference, or may be produced in accordance with known processes, i.e., analogously to known processes.
- the compounds of formula I and their physiologically acceptable salts exhibit interesting pharmacological activities in the eye and may therefore be used in accordance thereto. The compounds according to the invention are therefore useful for the treatment of ocular neovascularization.
- treatment refers to both prophylactic or preventive treatment as well as curative or disease-modifying treatment, including treatment of patients at risk of contracting the disease or suspected to have contracted the disease as well as patients who are ill or have been diagnosed as suffering from a disease or medical condition.
- the appropriate dosage will, of course, vary depending upon, for example, the compound employed, the host, the mode of administration and the nature and severity of the condition being treated. However, in general, satisfactory results in animals are indicated to be obtained at daily dosages from about 0.05 to about 50 mg/kg animal body weight.
- an indicated daily dosage may typically range from about 0.1 mg to about 100 mg, conveniently administered, for example, in divided doses up to four times a day.
- the compounds according to the invention may be administered by any conventional route, in particular enterally, orally, or topically, for example in the form of tablets, capsules or eye drops, or parenterally, for example in the form of injectable solutions or suspensions.
- the present invention furthermore provides a method of treating ocular neovascularization in a subject in need of such treatment, which comprises administering a therapeutically effective amount of a compound of formula (I).
- Ocular neovascularization is in particular referring to a medical condition which involves corneal, iris, choroidal, or retinal neovascularization (NV), age related macular degeneration, proliferative diabetic retinopathy, retinopathy of prematurity (ROP), ischemic retinopathy, and central vein occlusion.
- age related macular degeneration refers to both the dry and wet form of age related macular degeneration, the wet form being a preferred form. The following examples illustrate the invention.
- Capillary network formation in cultured HUVECs Various concentrations of compound A (0.1, 1, and 10 mM) are tested to assess the quality of effect of this compound on capillary networking (tube formation) in cultured human umbilical vein endothelial cells (HUVECs) seeded on growth factor-reduced Matrigel.
- the intensity of capillary networking is evaluated at 24 hours using a phase-contrast microscope. Images are captured and analySYS 3.2 software is used to count the number of tubes in five random fields of each well (8 wells altogether). The effect of the compound is compared to untreated cells grown in cell culture medium (control).
- Compound A significantly decreases the number of tubes at 1 mM and 10 mM concentrations as compared to the control group ( Figure 1).
- FIG. 1 illustrates the effect of compound A on capillary network formation in cultured HUVECs.
- compound A and related compounds are considered useful in the treatment of various ocular diseases that result from pathological angiogenesis, also called neovascularization (NV).
- NV neovascularization
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- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Ophthalmology & Optometry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention provides methods and uses of imidazolylalkyl-pyridines in the treatment of ocular disorders. A first aspect of the invention provides a method of treating ocular neovascularization comprising administering to a subject in need of such treatment a therapeutically effective amount of a compound having the formula (I) in free base or physiologically acceptable acid addition salt form, wherein R1.is hydrogen, lower alkyl, halogen with an atomic number of 9 to 35 or amino optionally mono- or disubstituted by lower alkyl, R2. and R3. independently of one another are hydrogen or lower alkyl, R4. is hydrogen, hydroxy, lower alkyl, lower alkoxy or halogen with an atomic number of 9 to 35, and the bridge between the pyridine and the imidazole, illustrated as methylene, is methylene or ethylene.
Description
ORGANIC COMPOUNDS
CROSS REFERENCE TO RELATED APPLICATIONS The current application claims the benefit of co-pending United Kingdom Patent Application No. GB 0402100.2, filed 30 January 2004, which is hereby incorporated herein by reference.
BACKGROUND OF THE INVENTION The present invention relates to the use of certain imidazolylalkyl-pyridines in the treatment of ocular disorders. More particularly, the present invention relates to the use of compounds of formula I,
wherein Rj. is hydrogen, lower alkyl, halogen with an atomic number of 9 to 35 or amino optionally mono- or disubstituted by lower alkyl, R2. and R3. independently of one another are hydrogen or lower alkyl, R4. is hydrogen, hydroxy, lower alkyl, lower alkoxy or halogen with an atomic number of 9 to 35, in free base or acid addition salt form, and the bridge between the pyridine and the imidazole, illustrated as methylene, is methylene or ethylene.
SUMMARY OF THE INVENTION The present invention provides methods and uses of imidazolylalkyl-pyri dines in the treatment of ocular disorders. A first aspect of the invention provides a method of treating ocular neovascularization comprising administering to a subject in need of such treatment a therapeutically effective amount of a compound having the formula (I) in free base or physiologically acceptable acid addition salt form,
wherein Rj. is hydrogen, lower alkyl, halogen with an atomic number of 9 to 35 or amino optionally mono- or disubstituted by lower alkyl, R2. and R3. independently of one another are hydrogen or lower alkyl, R4. is hydrogen, hydroxy, lower alkyl, lower alkoxy or halogen with an atomic number of 9 to 35, and the bridge between the pyridine and the imidazole, illustrated as methylene, is methylene or ethylene. A second aspect of the invention provides a use of a compound of formula (I) in the manufacture of a medicament for the treatment of ocular neovascularization, said compound of formula (I) being
wherein Rj. is hydrogen, lower alkyl, halogen with an atomic number of 9 to 35 or amino optionally mono- or disubstituted by lower alkyl, R2. and R3. independently of one another are
hydrogen or lower alkyl, ^. is hydrogen, hydroxy, lower alkyl, lower alkoxy or halogen with an atomic number of 9 to 35, and the bridge between the pyridine and the imidazole, illustrated as methylene, is methylene or ethylene.
BRIEF DESCRIPTION OF THE DRAWINGS Figure 1 illustrates the effect of a compound of the present invention on capillary network formation in cultured human umbilical vein endothelial cells (HUVECs).
DETAILD DESCRIPTION OF THE INVENTION As used herein lower in the context with alkyl and alkoxy groups denote a radical having up to 7 carbon atoms, preferably up to 4 carbon atoms and more preferably up to 2 carbon atoms. Consequently, lower alkyl has especially up to 7 carbon atoms, preferably up to 4 carbon atoms, and in particular up to 2 carbon atoms and is, for example, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, or hexyl. Accordingly, lower alkoxy has up to 7 carbon atoms, preferably up to 4 carbon atoms, and in particular up to 2 carbon atoms and is, for example, methoxy, ethoxy, propoxy, butoxy, tert-butoxy or hexyloxy. Insofar as above-defined lower alkyl or lower alkoxy groups are present in the compounds of formula (I), these preferably have one or two carbon atoms and especially signify methyl or methoxy. The imidazolylmethyl radical is preferably in position 2 of the pyridine. Rj is preferably methyl or ethyl, more preferably methyl. R and R3 are preferably each hydrogen. R» is preferably methyl, ethyl or hydrogen, more preferably methyl or hydrogen, and in particular hydrogen. The compound A of Example 1 is strongly preferred. In a particular group of compounds of formula (I), Rj is lower alkyl, R2 and R3 independently of one another are hydrogen or lower alkyl, and t is hydrogen, lower alkyl or halogen with an atomic number of 9 to 35.
In a further particular group of compounds of formula (I), Ri is methyl, R2 and R3 independently of one another are hydrogen or methyl, and R) is hydrogen, methyl or halogen with an atomic number of 9 to 35. Halogen with an atomic number of 9 to 35 denote in particular a fluorine and chlorine residue, more particularly a chlorine residue. The compounds of formula (I) may be present in free base form or in the form of their acid addition salts, including, for example, hydrogen fumarate and fumarate salt forms. Acid addition salts may be produced from the free bases in known manner, and vice versa. The compounds of formula (I) are known, e.g., from US 5,856,343 and US 5,635,521, which are incorporated herein by reference, or may be produced in accordance with known processes, i.e., analogously to known processes. The compounds of formula I and their physiologically acceptable salts exhibit interesting pharmacological activities in the eye and may therefore be used in accordance thereto. The compounds according to the invention are therefore useful for the treatment of ocular neovascularization. As used herein the terms "treatment" or "treat" refer to both prophylactic or preventive treatment as well as curative or disease-modifying treatment, including treatment of patients at risk of contracting the disease or suspected to have contracted the disease as well as patients who are ill or have been diagnosed as suffering from a disease or medical condition. For the indications as described herein, the appropriate dosage will, of course, vary depending upon, for example, the compound employed, the host, the mode of administration and the nature and severity of the condition being treated. However, in general, satisfactory results in animals are indicated to be obtained at daily dosages from about 0.05 to about 50 mg/kg animal body weight. In larger mammals, for example humans, an indicated daily
dosage may typically range from about 0.1 mg to about 100 mg, conveniently administered, for example, in divided doses up to four times a day. The compounds according to the invention may be administered by any conventional route, in particular enterally, orally, or topically, for example in the form of tablets, capsules or eye drops, or parenterally, for example in the form of injectable solutions or suspensions. The present invention furthermore provides a method of treating ocular neovascularization in a subject in need of such treatment, which comprises administering a therapeutically effective amount of a compound of formula (I). Ocular neovascularization is in particular referring to a medical condition which involves corneal, iris, choroidal, or retinal neovascularization (NV), age related macular degeneration, proliferative diabetic retinopathy, retinopathy of prematurity (ROP), ischemic retinopathy, and central vein occlusion. As used herein age related macular degeneration refers to both the dry and wet form of age related macular degeneration, the wet form being a preferred form. The following examples illustrate the invention.
Example 1
Compound A: [2-(2-methylimidazol-l-yl)methyl]pyridine (See, e.g., US 5,856,343)
9.7 g (75 mM) of 2-(chloromethyl)pyridine and 42 g (512 mM) of 2- methyl-imidazole are suspended in 40 ml dimethylformamide, then stirred for 3 hours at 105 °C. The dimethylformamide is distilled off and the crystalline residue is diluted with ethyl acetate and a little hexane. Following filtration, the mother solution is concentrated by evaporation and the dimethylformamide distilled off, and then shaken out several times between water and methylene chloride. 10.3 g of the oily title compound are obtained.
Capillary network formation in cultured HUVECs Various concentrations of compound A (0.1, 1, and 10 mM) are tested to assess the quality of effect of this compound on capillary networking (tube formation) in cultured human umbilical vein endothelial cells (HUVECs) seeded on growth factor-reduced Matrigel. The intensity of capillary networking is evaluated at 24 hours using a phase-contrast microscope. Images are captured and analySYS 3.2 software is used to count the number of tubes in five random fields of each well (8 wells altogether). The effect of the compound is compared to untreated cells grown in cell culture medium (control). Compound A significantly decreases the number of tubes at 1 mM and 10 mM concentrations as compared to the control group (Figure 1). The inhibitory effect of this compound is not related to cell toxicity as this is excluded by an additional study using ToxiLight kit (Cambrex), which is a very sensitive assay based on ATP release from damaged cells. Figure 1 illustrates the effect of compound A on capillary network formation in cultured HUVECs. In this figure the bars represent mean ± SD of the number of tubes per group; wells per group, n=8; *P<0.001, **P<0.0001 versus control. Based on the above finding, compound A and related compounds are considered useful in the treatment of various ocular diseases that result from pathological angiogenesis, also called neovascularization (NV).
Claims
CLAIMS 1. A method of treating ocular neovascularization comprising administering to a subject in need of such treatment a therapeutically effective amount of a compound having the formula (I) in free base or physiologically acceptable acid addition salt form,
wherein Rj. is hydrogen, lower alkyl, halogen with an atomic number of 9 to 35 or amino optionally mono- or disubstituted by lower alkyl; R2. and R3. independently of one another are hydrogen or lower alkyl; Rt. is hydrogen, hydroxy, lower alkyl, lower alkoxy or halogen with an atomic number of 9 to 35; and the bridge between the pyridine and the imidazole, illustrated as methylene, is methylene or ethylene.
2. The method of claim 1 which comprises administering the compound of Formula (I) wherein Rj is lower alkyl, halogen with an atomic number of 9 to 35 or amino optionally mono- or disubstituted by lower alkyl and the bridge between the pyridine and the imidazole is methylene.
3. The method of claim 2 wherein the compound administered is the compound of Formula (I) wherein Rj is methyl.
4. The method of claim 1 wherein the compound administered is in free base, hydrogen fumarate, or fumarate salt form.
5. The method of claim 1 wherein the compound administered is [2-(2-methylimidazol- l-yl-)methyl]pyridine, in free base or physiologically acceptable acid addition salt form.
6. The method of claim 5 wherein the compound administered is [2-(2-methylimidazol- l-yl)methyl]pyridine in free base, hydrogen fumarate, or fumarate salt form.
7. The method of claim 5 wherein the compound administered is [2-(2-methylimidazol- 1 -yl)methyl]pyridine fumarate.
8. The method of claim 1, wherein said ocular neovascularization is at least one of choroidal and retinal neovascularization.
9. The method of claim 1, wherein said ocular neovascularization is age related macular degeneration.
10. The method of claim 1, wherein said ocular neovascularization is proliferative diabetic retinopathy.
11. The method of claim 1 , wherein said ocular neovascularization is ischemic retinopathy.
12. The method of claim 1 wherein said method is for treating human or a mammal.
13. Use of a compound of Formula (I) in the manufacture of a medicament for the treatment of ocular neovascularization, said compound of formula (I) being
wherein Rj. is hydrogen, lower alkyl, halogen with an atomic number of 9 to 35 or amino optionally mono- or disubstituted by lower alkyl; R2. and R3. independently of one another are hydrogen or lower alkyl; Rt. is hydrogen, hydroxy, lower alkyl, lower alkoxy or halogen with an atomic number of 9 to 35; and the bridge between the pyridine and the imidazole, illustrated as methylene, is methylene or ethylene.
14. A method or use according to any of the preceding claims wherein said treatment is both prophylactic or preventive treatment as well as curative or disease-modifying treatment, including treatment of patients at risk of contracting the disease or suspected to have contracted the disease as well as patients who are ill or have been diagnosed as suffering from a disease or medical condition.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0402100.2A GB0402100D0 (en) | 2004-01-30 | 2004-01-30 | Organic compounds |
| PCT/US2005/003427 WO2005074926A1 (en) | 2004-01-30 | 2005-01-28 | Organic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP1718302A1 true EP1718302A1 (en) | 2006-11-08 |
| EP1718302A4 EP1718302A4 (en) | 2010-04-28 |
Family
ID=31971769
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP05712759A Withdrawn EP1718302A4 (en) | 2004-01-30 | 2005-01-28 | Organic compounds |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP1718302A4 (en) |
| GB (1) | GB0402100D0 (en) |
| WO (1) | WO2005074926A1 (en) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5635521A (en) * | 1991-09-23 | 1997-06-03 | Sandoz Ltd. | Imidazolylmethyl-pyridines |
| US20020006967A1 (en) * | 1997-06-19 | 2002-01-17 | Peter A. Campochiaro | Methods of treatment of ocular neovascularization |
| CN1198803C (en) * | 1999-03-05 | 2005-04-27 | 第一三得利制药株式会社 | Heterocyclic compounds having effect of activating nicoting acetylchloine alpha 4 beta 2 receptor |
| WO2002039954A2 (en) * | 2000-11-20 | 2002-05-23 | Smithkline Beecham Corporation | Novel compounds |
| US20020183253A1 (en) * | 2001-02-22 | 2002-12-05 | Brazzell Romulus Kimbro | Method of treating ocular neovascularization |
-
2004
- 2004-01-30 GB GBGB0402100.2A patent/GB0402100D0/en not_active Ceased
-
2005
- 2005-01-28 EP EP05712759A patent/EP1718302A4/en not_active Withdrawn
- 2005-01-28 WO PCT/US2005/003427 patent/WO2005074926A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP1718302A4 (en) | 2010-04-28 |
| GB0402100D0 (en) | 2004-03-03 |
| WO2005074926A1 (en) | 2005-08-18 |
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