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Use of vitamin D compounds for the prevention of adhesions

A compound, vitamin technology, applied to vitamin D compounds in the field of preventing adhesion

Inactive Publication Date: 2009-09-23
BIOXELL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] In general, existing methods of treating adhesions have had only limited success

Method used

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  • Use of vitamin D compounds for the prevention of adhesions
  • Use of vitamin D compounds for the prevention of adhesions
  • Use of vitamin D compounds for the prevention of adhesions

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 42-50

[0448] Table 1

[0449]

[0450] compound

X

Z

Y

A

B

1,25-dihydroxy-20-cyclopropyl-26,27-hexa

Deutero-19-nor-cholecalciferol

H 2

Oh

Oh

-

-

1,3-Di-O-acetyl-1,25-dihydroxy

-20-cyclopropyl-26, 27-hexadeuterio-19-nor-

Cholecalciferol

H 2

OAc

OAc

-

-

1,25-dihydroxy-20-cyclopropyl-26,27-hexa

Deutero-cholecalciferol

CH 2

Oh

Oh

-

-

1,3-Di-O-acetyl-1,25-dihydroxy

-20-cyclopropyl-26,27-hexadeuterio-cholecalcification

Alcohol

CH 2

OAc

OAc

-

-

1α-fluoro-25-hydroxy-20-cyclopropyl-26,27-

Hexadeuterio-cholecalciferol

CH 2

Oh

F

-

-

3-O-acetyl-1α-fluoro-25-hydroxy-20-

cyclopropyl-cholecalciferol

CH 2

OAc

F

...

Embodiment 1

[0515] Synthesis of 1-α-fluoro-25-hydroxy-16,23E-diene-26,27-dihomo-20-epi-cholecalciferol

[0516] tert-butyl-dimethyl-(4-methylene-3-{2-[7a-methyl-1-(1,4,5-trimethyl-hex-2-enyl)-octahydro- Inden-4-ylidene]-ethylidene}-cyclohexyloxy)-silane

[0517]

[0518] To the stirred 4-methylene-3-{2-[7a-methyl-1-(1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-ylidene Base]-ethylidene}-cyclohexanol (100.00g, 0.25mol) in DMF (250mL) was added continuously imidazole (40.80g, 0.6mol) and (tert-butyldimethyl)silyl chloride ( 45.40 g, 0.3 mol). The reaction mixture was stirred at room temperature for 1 hour, diluted with hexane (750 mL), washed with water (500 mL), 1N HCl (500 mL), brine (500 mL) and washed with Na 2 SO 4 dry. The residue (155 g) after evaporation of the solvent was filtered through a silica gel column (500 g, 5% AcOEt in hexane) to give the title compound (115.98 g, 0.23 mol, 92%).

[0519] 1 H-NMR: δ0.04 and 0.08 (2s, 6H), 0.59 (s, 3H), 0.90 (d, 3H, J=6.6Hz), 0.92...

Embodiment 2

[0667] Synthesis of 21-(3-hydroxy-3-methylbutyl)-1,25-dihydroxy-19-nor-cholecalciferol

[0668] [1R-[1α(2E,4E,7E),3aβ,4α,7aα]]-5-[4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]octahydro -7a-Methyl-1H-inden-1-yl]-2,4,7-diethyl nonatrienedioate

[0669]

[0670] To stirred 3.08g (10.0mmol) of [1R-(1α, 3aβ, 4α, 7aα)]-(1,1-dimethylethyl)dimethyl[[octahydro-7a-methyl-1 -(1-methylvinyl)-1H-inden-4-yl]oxy]silane and 3.92g (40.0mmol) of ethyl propiolate in 20mL of dichloromethane were added 40mL (40.0mmol) of 1.0M A solution of ethyl aluminum dichloride in hexane. The mixture was stirred at room temperature under argon for 24 hours, treated with 981 mg (10 mmol) of ethyl propiolate and 7.5 mL (7.5 mmol) of 1.0 M ethylaluminum dichloride in hexane and stirred for a further 18 hours . The resulting orange-red solution was added in portions to a mixture of 200 mL ethyl acetate and 100 mL of 50% brine, and after the hissing subsided, the organic phase was collected and the aqueous phase...

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Abstract

There is provided a method of prevention of adhesions, e. g. surgical adhesions, which comprises using a vitamin D compound.

Description

field of invention [0001] The present invention relates to new uses and methods as well as compounds for said uses, in particular the use of vitamin D compounds in the prevention of adhesions. Background of the invention [0002] An important clinical problem related to peritoneal and other tissue repair is the formation of adhesions. Adhesions form when closely adjacent surfaces are injured, for example due to surgical trauma, mechanical injury, ischemic injury, inflammation, chemical injury, radiation therapy, infection, or other foreign body reactions. [0003] A particularly important cause of adhesions is due to surgery. The formation and reformation of intra-abdominal adhesions after surgery is an important cause of morbidity. Adhesions after surgery can lead to intestinal obstruction. Adhesions caused by previous surgical procedures can increase the number of operations and complications during surgery, including damage and bleeding of the bowel, bladder, and urete...

Claims

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Application Information

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IPC IPC(8): A61K31/59
Inventor E·科利M·马里亚尼P·帕尼纳
Owner BIOXELL
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