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Compounds with growth hormone releasing properties

A compound and drug technology, applied in the field of new compounds, can solve the problem of inappropriate administration methods, and achieve the effect of increasing the release

Inactive Publication Date: 2007-03-14
NOVO NORDISK AS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In conditions or diseases in which elevated levels of growth hormone are desired, the proteinaceous nature of growth hormone makes any route of administration other than enteral administration unsuitable

Method used

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  • Compounds with growth hormone releasing properties
  • Compounds with growth hormone releasing properties
  • Compounds with growth hormone releasing properties

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0364] (2E)-5-amino-5-methylhex-2-enoic acid N-((1R)-1-{N-[(1R)-1-benzyl-2-(4-((dimethylamino )-methyl)piperidin-1-yl)-2-oxyethyl]-N-methylcarbamoyl}-2-(2-naphthyl)ethyl)-N-formamide;

[0365]

[0366] tert-Butyl 4-(dimethylcarbamoyl)piperidine-1-carboxylate

[0367]

[0368] 1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (8.0 g; 35 mmol) was dissolved in dichloromethane (70 ml) and N,N-dimethylformamide (35 ml). 1-Hydroxy-7-azabenzotriazole (4.75 g, 35 mmol) was added. The solution was cooled to 0 °C. N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (6.69 g; 35 mmol) was added. The reaction mixture was stirred at 0 °C for 20 minutes. A 5.6M solution of dimethylamine in ethanol (37ml, 209mmol) was added. The reaction mixture was stirred for 3 days while it was warmed to room temperature. It was diluted with ethyl acetate (400ml) and washed with 10% aqueous sodium bisulfate (400ml). The aqueous phase was extracted with ethyl acetate (2 x 200ml...

Embodiment 2

[0405] (2E)-5-amino-5-methylhex-2-enoic acid N-((1R)-1-{N-[(1R)-1-benzyl-2-((3S)-3-( Dimethylaminomethyl)piperidin-1-yl)-2-oxyethyl]-N-methylcarbamoyl}-2-(2-naphthyl)ethyl)-N-formamide

[0406]

[0407] (3R)-Piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

[0408]

[0409] 3-nipetcotate (R)-ethyl tartrate (10.0 g; 32.5 mmol) was suspended in tetrahydrofuran (90 ml). 1N Aqueous sodium hydroxide solution (98ml, 98mmol) was added. A solution of di-tert-butyl dicarbonate (7.10 g, 32.5 mmol) dissolved in tetrahydrofuran (90 mL) was added. The reaction mixture was stirred at room temperature for 16 hours. Ethyl acetate (400ml) was added. The reaction mixture was washed with 10% aqueous sodium bisulfate (400ml). The aqueous solution was extracted with ethyl acetate (2 x 200ml). The combined organic layers were washed with saturated aqueous sodium bicarbonate (200 ml) and dried over magnesium sulfate. Solvent was removed in vacuo. The crude product was ...

Embodiment 3

[0449] (2E)-4-(1-Aminocyclobutyl)but-2-enoic acid N-((1R)-1-{N-[(1R)-1-benzyl-2-((3S)-3 -(Dimethylaminomethyl)piperidin-1-yl)-2-oxyethyl]-N-methylcarbamoyl}-2-(2-naphthyl)ethyl)-N-formamide

[0450]

[0451] (1-{(2E)-3-[N-((1R)-1-{N-[(1R)-1-benzyl-2-((3S)-3-((dimethylaminomethyl) Piperidin-1-yl)-2-oxyethyl]-N-methylcarbamoyl}-2-(2-naphthyl)ethyl)-N-methylcarbamoyl]allyl}cyclobutane base) tert-butyl carbamate

[0452]

[0453] N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (85 mg, 0.44 mmol) was added to (2E)-5-(tert-butoxycarbonyl )-5-methylhex-2-enoic acid (113mg, 0.44mmol) and 1-hydroxyl-7-azabenzotriazole (60mg, 0.44mmol) were dissolved in dichloromethane (5ml) and N, N- Dimethylformamide (5ml) was added to the resulting solution. The reaction mixture was stirred at 0°C for 20 minutes. (2R)-N-[(1R)-1-benzyl-2-((3S)-3-((dimethylamino)methyl)piperidin-1-yl)-2-oxyethyl] was added sequentially -N-Methyl-2-(methylamino)-3-(2-naphthyl)propionamide (228mg...

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Abstract

The invention relates to novel compounds, compositions containing them, and their use for treating medical disorders resulting from a deficiency in growth hormone.

Description

field of invention [0001] The present invention relates to novel compounds, compositions containing them and their use in the treatment of medical conditions resulting from growth hormone deficiency. Background of the invention [0002] Growth hormone is a hormone that stimulates the growth of all tissues capable of growing. Growth hormone is also known to have many effects on metabolic processes, such as stimulating protein synthesis and free fatty acid mobilization and converting energy metabolism from carbohydrates to fatty acid metabolism. Growth hormone deficiency can lead to a number of serious medical conditions, such as dwarfism. [0003] Growth hormone is released from the pituitary gland. This release is under the tight control, directly or indirectly, of a number of hormones and neurotransmitters. Growth hormone-releasing hormone (GHRH) stimulates the release of growth hormone, while somatostatin inhibits the release of growth hormone. In both cases, the hormo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K14/60C07K5/02C07K5/06A61K38/05A61K38/25A61P5/02A61P5/04A61P5/06A61K38/00A61K38/22A61P29/00A61P43/00C07K5/065
CPCC07K5/0207A61K38/00A61P29/00A61P43/00A61P5/02A61P5/04A61P5/06C07K14/46C07K5/00
Inventor 伯恩德·佩施科斯蒂芬·L·里克特托马斯·K·汉森迈克尔·安克森
Owner NOVO NORDISK AS
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