Meiosis regulating compounds

A compound and hydroxyl technology, applied in the direction of steroids, medical preparations containing active ingredients, organic chemistry, etc., can solve problems such as compounds not mentioned

Inactive Publication Date: 2000-01-19
NOVO NORDISK AS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0030] The above-mentioned documents do not mention compounds capable of regulating meiosis, and the contents of the above-mentioned documents are hereby incorporated by reference,

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0244] In the oocyte test, cholest-5-ene-3β,4β-diol was tested as a meiosis activating substance.

[0245] animal

[0246] Oocytes were obtained from immature female mice (C57BI / 6JxDBA / 2J F1-hybrid, Bomholtgaard, Denmark) weighing 13-16 g and reared under controlled light and temperature. Gonadotropin (Gonal-F.Serono, Solna, Sweden, containing 20 IU FSH, and Puregon, Organon, Swords, Ireland, containing 20 IU FSH) was injected intraperitoneally into the mice, and after 48 hours, the kill animals.

[0247] Oocyte collection and culture

[0248] Ovaries were dissected and oocytes were isolated by manual puncturing of follicles with a pair of 27 gauge needles under a stereomicroscope in Hx-medium (see below). Spherical oocytes with complete blastocysts were divided into cumulus-enclosed oocytes (CEO) and naked oocytes (NO) and placed in 3mM hypoxanthine (Sigma Cat.No.H-9377), 8mg / ml human serum albumin (HSA, StateSerum Institute, Denmark), 0.23mM pyruvate (Sigma Cat.No.S-8636...

Embodiment 2

[0258] In the oocyte assay, compounds are tested for inhibition of meiosis.

[0259] Blastocyst (GV) oocytes were obtained from immature FSH-treated female mice following the same method as described in Example 1 (supra). Oocytes were washed three times in Hx-medium, and oocytes of uniform size were divided into CEO and NO groups. 4,4-Dimethylcholesta-8,14,24-trien-3β-ol (FF-MAS) has previously been shown to induce meiosis of CEO and NO in test tubes (Byskov, A.G. et al., Nature 374 (1995) 559-562). In 4-well multiwell plates (Nunclon, Denmark), CEO and NO were co-incubated with different concentrations of test compounds in Hx-medium supplemented with 0.7-7.0 μM FF-MAS, wherein each well contained 0.4 ml of Hx-medium and 35-45 oocytes. Usually at the same time as experiments with test cultures supplemented with different concentrations of test compounds, experiments with a set of controls (i.e. 35-45 oocytes cultured in Hx-medium containing FF-MAS without the addition of te...

Embodiment 3

[0266] 4,4-Dimethylcholesta-5,8-dien-3-one

[0267] The D-8 double bond was introduced according to the method described in the literature [J. Lip. Res. 37, 1529, (1996)]. According to the method in the literature, cholesta-5,8-dien-3β-alcohol was prepared according to the 3-step method, and the alcohol was oxidized with the classic Oppenauer oxidation [Hev. Sta-4,8-dien-3-one, which was used as a starting material for some of the compounds listed below.

[0268] Potassium tert-butyrate (550 mg) was dissolved in 13 ml of 45°C tert-butanol, and a solution of cholesta-4,8-dien-3-one (470 mg) dissolved in 1.5 ml of tetrahydrofuran was added dropwise. After 10 minutes, iodomethane (0.63ml) was added and the reaction mixture was stirred for 1 hour. After treatment with water and purification by column chromatography, 4,4-dimethyl-cholesta-5,8-dien-3-one (310 mg) was isolated.

[0269] 1 H-NMR (CDCl 3 ): δ=0.64ppm(s, 3H, H-18); 0.86(2×d, J=7Hz, 6H, H-26 / 27); 0.94(d, J=7Hz, 3H, ...

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PUM

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Abstract

Certain compounds, structurally related to natural compounds which can be extracted i.e. from bull testes and from human follicular fluid, can be used for regulating the meiosis in oocytes and in male germ cells.

Description

field of invention [0001] The present invention relates to pharmacologically active compounds and their use as medicines. More specifically, it has been found that the sterol derivatives described herein can be used to regulate meiosis. Background of the invention [0002] 5α-bromocholestane-3β,6β-diol, 7α-bromocholestane-3β,6α-diol, 7α-bromocholestane-3β, 6β-diol, 7α-bromocholestane-3β, 5α-diol-6-one, 7β-bromocholestane-3β, 5α-diol-6 -ketone, 3β-bromocholestan-2α-ol, 5α-chlorocholestane-3β, 6α-diol, 5α-chlorocholestane-3β, 6β-diol, 6β-chlorocholestane Steranes-3β, 5α-diol, Δ 7，9(11) -cholestadiene-3β,6α-diol, Δ 7，9(11) -cholestadiene-3β, 6β-diol, cholestane-2α, 3α-diol, cholestane-2α, 3β-diol, cholestane-2β, 3α-diol, cholestane- 2β, 3β-diol, cholestane-3α, 4α-diol, cholestane-3α, 4β-diol, cholestane-3β, 4β-diol, cholestane-3α, 5α-diol , cholestane-3β, 5α-diol, cholestane-3β, 6α-diol, cholestane-3β, 6β-diol, cholestane-3β, 22α-diol, cholestane-3β , 22β-diol, cholestan...

Claims

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Application Information

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IPC IPC(8): A61K31/575C07J9/00
Inventor 克里斯琴・格朗达尔弗雷德里克・C・格朗维尔德彼得・法鲁普安东尼・默里简・L・奥特森
Owner NOVO NORDISK AS
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