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1-(1- (2-Ethoxyethyl)-3-Ethyl-7-(4-Methylpyridin-2-Ylamino) - 1H-Pyrazolo [4,3-D] Pyrimidin-5-YL) Piperidine-4-Carboxylic acid and salts thereof

a technology of piperidine and carboxylic acid, which is applied in the field of piperidine4carboxylic acid and its salts, and can solve the problems that not all patients respond to such drugs as effectively or as safely as desired

Inactive Publication Date: 2009-06-18
PFIZER INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0008]In another embodiment, the invention comprises a pharmaceutical composition comprising 1-(1-(2-ethoxyethyl)-3-ethyl-7-(4-methylpyridin-2-ylamino)-1H-pyrazolo[4,3-d]pyrimidin-5-yl)piperidine-4-carboxylic acid, or a pharmaceutically acceptable salt thereof, one or more additional therapeutic agents, and a pharmaceutically acceptable carrier.
[0009]In another embodiment, the invention comprises methods for treating a condition in a subject by administering to a subject a therapeutically effective amount of 1-(1-(2-ethoxyethyl)-3-ethyl-7-(4-methylpyridin-2-ylamino)-1H-pyrazolo[4,3-d]pyrimidin-5-yl)piperidine-4-carboxylic acid, or a pharmaceutically acceptable salt thereof. Conditions that can be treated in accordance with the present invention include cardiovascular conditio

Problems solved by technology

Despite the numerous drugs available in various pharmacological categories to treat hypertension and related physiological problems, not all patients respond to such drugs as effectively or as safely as desired.

Method used

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  • 1-(1- (2-Ethoxyethyl)-3-Ethyl-7-(4-Methylpyridin-2-Ylamino) - 1H-Pyrazolo [4,3-D] Pyrimidin-5-YL) Piperidine-4-Carboxylic acid and salts thereof
  • 1-(1- (2-Ethoxyethyl)-3-Ethyl-7-(4-Methylpyridin-2-Ylamino) - 1H-Pyrazolo [4,3-D] Pyrimidin-5-YL) Piperidine-4-Carboxylic acid and salts thereof
  • 1-(1- (2-Ethoxyethyl)-3-Ethyl-7-(4-Methylpyridin-2-Ylamino) - 1H-Pyrazolo [4,3-D] Pyrimidin-5-YL) Piperidine-4-Carboxylic acid and salts thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0148]

1-(1-(2-ethoxyethyl)-3-ethyl-7-(4-methylpyridin-2-ylamino)-1H-pyrazolo[4,3-d]pyrimidin-5-yl)piperidine-4-carboxylic Acid

Step 1: Preparation of 1-(2-ethoxyethyl)-3-ethyl-4-nitro-1H-pyrazole-5-carboxamide

[0149]

[0150]A 1 L flask was charged with 3-ethyl-4-nitropyrazole-5-carboxamide (prepared as described in EP 1176142 at page 18) (15.0 g, 81 mmol), triphenylphosphine (25.6 g, 97.8 mmol), and tetrahydrofuran (120 mL). The resulting mixture was cooled by placing the flask in a 0° C. bath and 2-ethoxyethanol (9.5 ml, 98 mmol) was added to the flask. A solution of di-tert-butyl azodicarboxylate (22.5 g, 97.8 mmol) in tetrahydrofuran (90 mL) was then added to the flask over a period of 2.5 hours. The mixture was stirred with cooling for an additional hour and then warmed to room temperature and stirred for one additional hour. The mixture was again cooled to 0° C., treated with 6M hydrochloric acid (40 ml), and heated to 40° C. for one hour. The mixture was partially concentrated and...

example 2

[0162]

1-(1-(2-ethoxyethyl)-3-ethyl-7-(4-methylpyridin-2-ylamino)-1H-pyrazolo[4,3-d]pyrimidin-5-yl)piperidine-4-carboxylic Acid

Step 1: Preparation of 1-(2-ethoxyethyl)-3-ethyl-4-nitro-1H-pyrazole-5-carboxamide

[0163]

1-(2-ethoxyethyl)-3-ethyl-4-nitro-1H-pyrazole-5-carboxamide was prepared according to step 1, Example 1

Step 2: Preparation of 4-amino-1-(2-ethoxyethyl)-3-ethyl-1H-pyrazole-5-carboxamide

[0164]

[0165]A mixture of 1-(2-ethoxyethyl)-3-ethyl-4-nitro-1H-pyrazole-5-carboxamide from step 1 (5.70 g, 22 mmol) and palladium hydroxide (1.0 g) in ethanol (110 mL) was treated with ammonium formate (7.01 g, 111 mmol) in four unequal portions at about 10 minute intervals. The resulting mixture was heated under reflux for two hours and then cooled. The mixture was filtered through celite and concentrated. The resulting residue was purified by column chromatography on silica gel using a mixture of ethyl acetate and hexane as the eluent to provide 2.45 g of the title compound. 1H NMR (400 MHz...

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Abstract

The present invention comprises 1-(1-(2-ethoxyethyl)-3-ethyl-7-(4-methylpyridin-2-ylamino)-1H-pyrazolo[4,3-d]pyrimidin-5-yl)piperidine-4-carboxylic acid and its salts. The invention further comprises pharmaceutical compositions, methods of treatment, and synthetic methods relating to 1-(1-(2-ethoxyethyl)-3-ethyl-7-(4-methylpyridin-2-ylamino)-1H-pyrazolo[4,3-d]pyrimidin-5-yl)piperidine-4-carboxylic acid and its salts.

Description

FIELD OF THE INVENTION[0001]The present invention relates generally to 1-(1-(2-ethoxyethyl)-3-ethyl-7-(4-methylpyridin-2-ylamino)-1H-pyrazolo[4,3-d]pyrimidin-5-yl)piperidine-4-carboxylic acid and its salts. The present invention further relates to pharmaceutical compositions comprising this compound or its salts, methods of treatment employing this compound or its salts, and methods of preparing this compound or its salts. In general, the compound and its salts inhibit the cyclic guanylate monophosphate-specific phosphodiesterase type 5 (“PDE5”) enzyme.BACKGROUND OF THE INVENTION[0002]Hypertension is a condition associated with, among other physiological problems, an increased risk of stroke, myocardial infarction, atrial fibrillation, heart failure, peripheral vascular disease and renal impairment. Despite the numerous drugs available in various pharmacological categories to treat hypertension and related physiological problems, not all patients respond to such drugs as effectively...

Claims

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Application Information

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IPC IPC(8): A61K31/519C07D487/04A61P9/12A61P25/00A61P9/00
CPCC07D487/04A61P1/02A61P1/04A61P11/00A61P13/00A61P13/02A61P13/08A61P13/12A61P15/00A61P15/06A61P15/08A61P15/10A61P17/02A61P17/04A61P17/06A61P17/14A61P19/04A61P19/10A61P21/00A61P21/02A61P25/00A61P25/04A61P25/08A61P25/10A61P25/12A61P25/14A61P25/16A61P25/20A61P25/22A61P25/24A61P25/28A61P25/32A61P27/02A61P27/06A61P27/12A61P27/16A61P3/00A61P35/00A61P3/04A61P3/06A61P35/04A61P43/00A61P5/14A61P5/50A61P7/02A61P9/00A61P9/04A61P9/08A61P9/10A61P9/12A61P9/14A61P3/10A61K31/505
Inventor TOLLEFSON, MICHAEL B.
Owner PFIZER INC
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