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Compounds with growth hormone releasing properties

A compound, halogen technology, applied in the application field of medical diseases, can solve problems such as invalidity

Inactive Publication Date: 2001-03-21
NOVO NORDISK AS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In diseases or conditions in which increased growth hormone levels are desired, the proteinaceous properties of growth hormone render any administration other than parenteral ineffective

Method used

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  • Compounds with growth hormone releasing properties

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0176] (2E)-5-Amino-5-methylhex-2-enoic acid N-((1R)-1-(N-[(1R)-2-(N'-acetylhydrazino)-1-benzyl Base-2-oxoethyl]-N-methylcarbamoyl)-2-(2-naphthyl)ethyl)-N-methylamide

[0177] tert-Butyl N'-Acetylhydrazinocarboxylate

[0178] To a solution of tert-butyl carbazate (1.0 g, 7.6 mmol) and pyridine (3.1 ml) in dichloromethane (5 ml) was added acetic anhydride (1.5 ml) slowly and the mixture was stirred overnight. The mixture was added to dichloromethane (50ml) and washed with water (2 x 10ml) and brine (10ml) and dried (MgSO 4 ), filtered and concentrated in vacuo to afford 0.95 g of tert-butyl N'-acetylhydrazinecarboxylate as a yellow oil.

[0179] LC-MS:R t =5.39 minutes, m / z=349.6(m+1)

[0180] 1 H NMR (CDCl 3 ) Selected peak: δ1.5(s, 9H, (CH 3 ) 3 C-O); 2.05(s,3H,CH 3 CO)

[0181] N-[(1R)-2-(N'-acetylhydrazino)-1-benzyl-2-oxoethyl]-N-methylcarbamate tert-butyl ester

[0182] tert-Butyl N'-acetylhydrazinecarboxylate (0.95g, 5.45mmol) was dissolved in dichloromet...

Embodiment 2

[0200] (2E)-5-amino-5-methylhex-2-enoic acid N-((1R)-1-(N-[(1R)-2-(N'-acetyl-N-methylhydrazino )-1-benzyl-2-oxoethyl]-N-methylcarbamoyl)-2-(2-naphthyl)ethyl)-N-methylamide

[0201] N'-Acetyl-N-methylhydrazine carboxylate tert-butyl ester

[0202] To a solution of tert-butyl N-methylhydrazinecarboxylate (0.62g, 4.20mmol) dissolved in dichloromethane (10ml) was added acetic anhydride (0.79ml, 8.40mmol) and pyridine (1.36ml, 16.80mmol) And the mixture was stirred overnight. Dichloromethane (50ml) was then added and the mixture was washed with water (3 x 10ml), dried (MgSO 4 ), filtered and concentrated in vacuo to afford 0.32 g (41%) of tert-butyl N'-acetyl-N-methylhydrazinecarboxylate as an oil.

[0203] 1 H NMR (CDCl 3 ) Selected peak: δ1.45+1.48(2s,9H,(CH 3 ) 3 C-O, rotamers); 1.98(s,3H,COCH 3 ); 3.14+3.17(2s,3H,N-CH 3 , rotamer) N'-methylhydrazine acetate

[0204] To a solution of tert-butyl N'-acetyl-N-methylhydrazinecarboxylate (0.3 g, 1.59 mmol) in dichloro...

Embodiment 3

[0224] (2E)-5-Amino-5-methylhex-2-enoic acid N-((1R)-1-(N-[(1R)-2-(N'-acetyl-N'-methylhydrazine Base)-1-benzyl-2-oxoethyl]-N-methylcarbamoyl)-2-(2-naphthyl)ethyl)-N-methylamide

[0225] tert-Butyl N'-benzylidenehydrazinecarboxylate

[0226] To a solution of tert-butyl carbazate (10.0 g, 75.64 mmol) in 99% ethanol (100 mL) was added benzaldehyde (7.64 mL, 75.64 mmol) and the mixture was stirred for 60 minutes. The mixture was cooled to 0°C, filtered and the precipitate was washed with cold ethanol and dried to give 13.47 g (81%) of tert-butyl N'-benzylidenehydrazinecarboxylate as white crystals.

[0227] Mp 184-186°C

[0228] 1 H NMR (CDCl 3 ):δ1.52(s,9H,(CH 3 )C); 7.34-7.92 (m, 7H, aromatic hydrogen)

[0229] tert-butyl N'-benzylidene-N-methylhydrazinecarboxylate

[0230] To a solution of tert-butyl N'-benzylidenehydrazinecarboxylate (2.0g, 9.07mmol) dissolved in anhydrous tetrahydrofuran (20ml) was added iodomethane (4.54ml, 72.6mmol) and the solution was cooled ...

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Abstract

Compounds of general formula (I), 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 diseases caused by growth hormone deficiency. Background of the invention [0002] Growth hormone is a hormone that promotes the growth of all tissues capable of growing. In addition, growth hormone is known to exert diverse effects on metabolic processes, such as promoting protein synthesis and free fatty acid mobilization, and acting as a switch in energy metabolism of carbohydrate to fatty acid metabolism. Growth hormone deficiency can lead to several serious medical conditions, such as dwarfism. [0003] Growth hormone is released from the pituitary gland. This release is tightly regulated, directly or indirectly, by a number of hormones and neurotransmitters. Growth hormone release can be promoted by growth hormone releasing hormone (GHRH) and can be inhibited by somatostatin. In both cases, both hormones are released fro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K38/00A61K38/04A61P43/00C07K5/02C07K5/06C07K5/065C07K5/078C07K5/08C07K5/083
CPCC07K5/0806C07K5/0207C07K5/06078C07K5/06026A61P43/00A61P5/06C07K5/08
Inventor 迈克尔·安科森
Owner NOVO NORDISK AS
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