The way to obtain 11-ketosteroids derived

 

(57) Abstract:

The invention relates to a new method of obtaining 11-ketosteroid derivatives of General formula I, where R is H, acyl, C1- C8, R1- CH3CH2OR11, R11- H, acyl, C1- C8, 3-oxoprop protected in the form of atlanticocean consists in the fact that the compound of formula II is converted into gelegenheden formula III in the presence of alcohol, and the resulting product is treated with acid. 6 C.p. f-crystals.

The invention concerns a method of obtaining 11-ketosteroids derived.

In particular, the invention concerns a method for obtaining compounds of formula (I)

< / BR>
where

R is a hydrogen atom or the residue of a complex or a simple ester, R' is a methyl radical or the radical-CH2OR", and R" is the remainder of a complex or a simple ester, equal or different from R, and the cycles A and B mean group

< / BR>
where

K is an oxygen atom or a group protecting moiety 3-oxo of the formula where n is 2 or 3, and the dashed line may be the second link, which is what converts the compound of formula (II)

,

where

R and R' is defined above and cycles A' and B' or cycles A and B, such as they are defined in>n is defined above, and K is an alkyl radical with 1 to 8 carbon atoms and the alkyl radical with 6 to 12 carbon atoms, in gelegenheden formula (III)

< / BR>
where

X is a halogen atom and R, R', A' and B' are defined above, and characterized in that gelegenheden subjected to a rearrangement reaction in the presence of alcohol in order to obtain, after treatment with acid, the target compound of formula (I).

Under the halogen atom is preferably involve chlorine atom, bromine or iodine, and bromine is preferred.

When R and R" is the residue of ester, it is preferably the acyl radical with 1 to 8 carbon atoms and especially radical formyl, acetyl, propionyl, butyryl, valeryl or benzoyl.

When R and R" is a residue of the ester, preferably an alkyl radical with 1 to 6 carbon atoms, for example methyl, ethyl or propyl, radical tetrahydropyranyl or balance similarvideo ether, for example trialkylsilyl, such as trimethyl - or dimetil-tert-Boticelli, triallelic, for example triphenylsilane, or diarylethylenes, for example diphenylmethylsilane.

When K" is an alkyl radical, preferably it is a methyl radical or ethyl.

When K" is an aryl radical, it is preferably a phenyl radical.

Higher alcohol or polyhydric alcohol is preferably chosen in the group formed by glycerol, ethylene glycol and propylene glycol, and ethylene glycol is particularly preferred.

Preferably operate in the presence of alcohol or a polyhydric alcohol taken in excess, by heating at a temperature below 100oC. Under excess imply preferably from 10 to 20 equivalents.

In addition, it is expedient to work in the presence of co-solvent, inert under the reaction conditions, with a boiling point below 100oC and under reflux.

The co-solvent may be, for example, esters, such as ethyl ether, acetic acid, benzene or cyclohexane. Especially preferred ethyl ester of acetic acid.

Subsequent treatment with an acid is preferably aqueous mineral or organic acid, for example hydrochloric acid, hydrogen bromide, sulfuric, perchloric, nitric acid, paratoluenesulfonyl, acetic, formic, oxalic acid or an acidic resin.

The treatment with an acid, in particular, leads to the liberation of ketala, intermediate formed in the position 20 and, possibly, in position 3, under the action of(II), where cycles A' and B' are different from the cycles A and B and only in this case there is a release system 3-keto 4 or functions of 3-keto.

In particular, according to the invention using gelegenheden formula (III), where X is a bromine atom.

The invention also relates to a method, according to which use gelegenheden formula (III), where the cycles of A' and B' is a group of the formula

< / BR>
where

K and the dashed line in 4/5/ defined above.

According to the invention using gelegenheden formula (III), where R is chosen in the group formed by a hydrogen atom, an acyl radical with 1 to 8 carbon atoms, an alkyl radical with 1 to 6 carbon atoms, a radical tetrahydropyranyl and balance similarvideo simple ester and R' is a methyl radical or the radical-CH2-OR", where R" is the same or different from R, has R mentioned above.

The method of conversion of steroid-9-halo - 11-hydroxy in the production of 11-keto described in the technical literature (European patent 30368). According to this method, heat gelegenheden at elevated temperature (180 - 350oC almost 250 - 300oC) in the presence of an aprotic solvent with a high boiling point, in a short time (a few minutes).

The method according to the invention requires milder conditions, which is possible only when receiving the intermediate compounds, locked in place at the level of ketone functions. For information, we can say that due to the lock link uglevodorodnogo in position 9 becomes unstable, which facilitates the rearrangement and thus creates a very mild reaction conditions. In practice, the reaction is carried out at temperatures below 100oC in the presence of an appropriate co-solvent.

In the method according to European patent N 30368 not provided by the formation of intermediate compounds obtained in the method of the invention, and because of this, in the known method requires different reaction conditions, without which it does not lead to the desired result. Furthermore, it is obvious that this method, in which you briefly heated to high temperature gelegenheden, is unlikely to be implemented at industrial level, using the reagents in very large quantities. On the contrary, the method of the present invention easily allows the synthesis on an industrial scale. In addition, using milder conditions than those described in the European patent N 30368, created mainly is bicheno, thus is an advantage, because this synthesis becomes more economical on an industrial level.

Gelegenheden formula (III) are generally known or can be easily obtained by methods known in the art. As an example: J. A. C. S. 79 1135 (1957), USP 2 763 671, 2 852 511 or 2 963 498, BF 1 188 434, USP 3 100 210, 3 084 174 or 3 499 081, EP. 97 328 or 3341 or even DD 268 955. The compounds of formula (II) are also known or can be obtained by known methods.

The compounds of formula (I) are either known therapeutic active compounds or known intermediates for the preparation of therapeutically active compounds.

The following examples illustrate the invention but do not restrict it.

Example 1. 17-oxepin-4-ene-3,11,20-Trion.

Stage A. 9-bromo - 11-17- -dioxopregna-4-ene-3,20-dione.

In an inert gas mixed with 2 g of 17-oxepin a 4.9/11/-diene-3,20-dione and 10 cm3of tetrahydrofuran, and then added at 0oC 1.3 g of N-bromosuccinimide. Cooled to about -3oC, and then slowly added a mixture of 1.3 cm365% perchloric acid and 2.5 cm3water. Stand under stirring for 3 hours 30 minutes and then poured into 100 cmPotreblyaemoi in this form.

Stage B. 17-oxepin-4-ene-3,11,20-Trion.

In an inert mixed gas of 2.05 g of 9-bromo - 11-17-dioxopregna-4-ene-3,20-diode 14 cm3ethyl ester of acetic acid and 4.6 cm3of ethylene glycol. Heated under reflux for 16 hours, and then cooled to 20oC. Add 3.2 cm3of concentrated hydrochloric acid and 35 cm3water, and then stirred for 20 hours. Then redistilled ethyl ester of acetic acid under reduced pressure and added 7 g of sodium chloride. Stirred for 30 minutes at 20oC, and then sucked off the crystals and wash them in salt water. These crystals take in methylene chloride, dried solution and concentrate to dryness. The remainder chromatographic on silicon dioxide, elwira a mixture of methylene chloride - ethyl ester acetic acid (8-2) and obtain 1.26 g of the target product.

IR-spectrum /CHCl3/: Absorption at 3610 cm-1/OH/; 1706-1667 cm-1(conjugated ketone) 1617 cm-1/C=C/.

Example 2. 17-acetamiprid-4-ene-3,11,20-Trion.

Stage A. 9-bromo - 11-hydroxy 17-acetamiprid-4-ene-3,20-dione.

In an inert atmosphere mixed with 3.7 g of 17-acetoxyphenyl 4,9 (11)-diene-3,20-dione and 18.5 cm3of tetrahydrofuran and then cooled to 0o/ - 5oC etc>
water, and then stirred for 1 hour. Then poured into 100 volumes of a mixture of water-ice, filtered, the crystals washed with water and dried. Get 4,82 g of the target product.

Range of IR /CHCl3/: Absorption at 3612 cm-1/OH/; 1731 cm-1/OAc/; 1716 and 1354 cm-1/-CO-CH3/; 1662 and 1621 cm-1/ 4,3-it/.

Stage B. 17-acetamiprid-4-ene-3,11,20-Trion.

In an inert gas heated to reflux 1 g obtained in stage a product, 7 cm3ethyl ester of acetic acid and 2.3 cm3of ethylene glycol. Maintain reflux for 24 hours, and then cooled to 20oC and add 1.6 cm3of concentrated hydrochloric acid and 17.5 cm3water. Stirred for 16 hours, and then distilled under reduced pressure, ethyl ester acetic acid. Saturated with sodium chloride and extracted with methylene chloride. The organic layer was washed with saturated aqueous sodium bicarbonate and then with water, saturated sodium chloride, and dried. Concentrate to dryness and the residue chromatographic on silicon dioxide, elwira a mixture of methylene chloride - ethyl ester acetic acid /9-1/. Obtain 0.51 g of the target product, which precrystallizer in ethanol.

The IR spectrum /CHCl3Cl3, 259 MHz, ppm/: 0,63 /S/ : 18-CH3; 1,42 /S/ : 19-CH3; 2,03 /S/ and 2.15 /S/ : CO-CH3; 5,74 /S/ : H4.

Example 3. 17-hydroxy 21-acetamiprid-4-ene-3,11,20-Trion.

Stage A. 9-bromo - 11,17-deoxy 21-acetamiprid-4-ene-3,20-dione.

In an inert gas mixed 4.71 g of 17-hydroxy-21-acetoxyphenyl a 4.9/11/-diene-3,20-dione and 65 cm3of tetrahydrofuran, and then added at 0o/ -5oC 3,26 g of N-bromosuccinimide, and then slowly a mixture of 2.6 cm370% perchloric acid and 5.2 cm3water. After 1 hour and 15 minutes with stirring at 0o/ -5oC pour a solution of 50 volume mixture of water-ice, filtered off, washed crystals with water, and then dried them. Get of 5.89 g of the target product.

IR-spectrum /CHCl3/ : Absorption at 1743 - 1722 cm-1/-CO-CH2OAc/; 1628 cm-1/ 4,3-keto/; Integrated absorption area /OH/ NH/.

Stage B. 17-hydroxy 21-acetamiprid-4-ene-3,11,20-Trion.

In an inert gas mixed 0.7 g obtained in stage a product, 4.9 cm3ethyl ester of acetic acid and 1.6 cm3of ethylene glycol. Heated with reflex 5 hours and 15 minutes, and then cooled to 20oC and add 1.1 cm3of concentrated hydrochloric acid and 12.2 cm3water. Videris the hydrated layer is saturated with sodium chloride, and then crystals are sucked off, washed with water, saturated sodium chloride and then dried. The product absorb a mixture of chloroform-isopropanol /97-3/, filtered and chromatographic the filtrate on silica, elwira a mixture of chloroform-isopropanol /97-3/. Get to 0.23 g of the target product.

IR-spectrum /CHCl3/: Absorption at 3610 cm-1/OH/; 1748, 1730, 1707 and 1667 cm-1/C=C/.

Example 4. 17 , 21-oxepin-4-ene-3,11,20-Trion /cortisone/.

Stage A: 9-bromo-11,17, 21-trioxepane-4-ene-3,20-dione.

In the inert gas are mixed at 0o/-5oC 4,2 g 17 , 21-dioxopregna of 4.9/11/-diene-3,20-dione and 46 cm3tetrahydrofuran (THF). Add 3,26 g of N-bromosuccinimide, and then slowly a mixture of 2.6 cm370% perchloric acid and 5.2 cm3water. After 1 hour 15 minutes at 0o/-5oC pour a solution of 50 volume mixture of water-ice. Filter, wash the crystals with water and dried. Get a 4.86 g of the target product.

IR-spectrum /liquid Paraffin/ : Absorption at 1710 cm-1/unpaired ketone/, 1663 and 1618 cm3/conjugated ketone/, the absorption region OH/ NH/.

Stage B: 17 ,21-oxepin-4-ene-3,11,20-Trion.

In an inert gas mixed 0.7 g obtained in stage a product, 4.9 cm3oC and add 1.1 cm3of concentrated hydrochloric acid and 12.2 cm3water. Stirred for 16 h, and then distilled ethyl ester of acetic acid under reduced pressure. Saturated with sodium chloride and extracted with methylene chloride, washed with saturated aqueous sodium bicarbonate solution the organic layer, and then saturated aqueous sodium chloride, dried and concentrated to dryness. The remainder chromatographic on silicon dioxide, elwira a mixture of chloroform-isopropanol (92,5 - 7,5). Obtain 0.11 g of the target product, which can be cleared by dissolving in a mixture of methylene chloride - isopropyl ether and fending off the methylene chloride. The desired product crystallizes.

IR spectrum (liquid Paraffin): Absorption at 3480 cm-1(OH); 1700 cm-1(11 and 20 keto); 1650 cm-1(conjugated ketone); 1613 cm-1(C=C).

Example 5. Obtaining cyclic 3-[(1,2-ethandiyl)mercapto]- - 17-hydroxy-21-acetamiprid-4-ene-3,11,20-trione.

Stage A. Cyclic 3-[(1,2-ethandiyl)mercapto]- 9-bromo- - 11-17-deoxy-21-acetamiprid-4-ene-3,20-dione.

Work on the methodology stage a of example 3 of the application on the basis of 4.4 g of cyclic 3-[(1,2-ethandiyl)-mercapto]- 17-hydroxy-21- -acetoxyphenyl of 4.9/11/-Dien-3,30-Dion>Ac). Region absorption OH/NH.

The original product was obtained as follows.

Mix in the atmosphere of inert gas at 20oC 100 cm3methanol is 6.4 g of 17-hydroxy-1-acetoxyphenyl of 4.9/11/-diene-3,20-dione, 1.8 cm3ethicial and 2.5 cm3epirate boron TRIFLUORIDE. Stirred for 2 hours and the solvent is evaporated. Treated with methylene chloride, washed with saturated aqueous sodium bicarbonate, water and dried. Is evaporated to dryness and obtain 7.9 g of the target product, used as such in the example above.

IR-spectrum /CHCl3/: No 3-keto - -4; absorption at 1745-1730 cm-1/-CO-CH2OAc/; region absorption OH/NH; the absorption at 1610 cm-1/ 9,11/.

Stage: Obtaining cyclic -[(1,2-ethandiyl)mercapto] 17-hydroxy-21-acetamiprid-4-ene-3,11,20-trione.

Working on a technique similar to the method steps In example 3, using as starting product of 0.48 g of the product obtained in stage a above. After purification by chromatography on silica, elwira a mixture of toluene-isopropanol 95/5, obtain 0.3 g of the target product.

IR spectrum (CHCl3): Absorption at 1646 cm-1(C=C), 1749, 1729 and 1706 cm-1(C=O /OAc, 20-keto, 11-keto), 3608 cm>; 2,17 /c/: OAc; 2,54 /c/: OH; 3,15 - 3,40: thioketal; with 4.64 /e J = 17,5/; 5,13 /e J = 17,5/; CO-CH2O; 5,55 /d/ : H4.

Example 6. Getting 17-oxepin-4-ene-3,11,20-trione rearrangement in n-butanol.

Mix 1.5 g of 9-bromo-11 11,17-dioxopregna-4-ene-3,20-dione and 15 cm3n-butanol in an atmosphere of inert gas and refluxed for 3.5 hours the Solution is allowed to cool. Target product slowly precipitates. Filtered and washed with isopropanol and a mixture of isopropyl ether and isopropanol, and then dried. Get to 0.67 g of the target product. The product was then purified by boiling under reflux in ethyl ether and after filtration and drying receive 0,585 g of the target product, the title of which is determined by HPLC. He is 91,5 %, which corresponds to 0.53 g of pure product.

Example 7. Getting 17-oxepin-4-ene-3,11,20-trione rearrangement in n-propanol.

Work on the methodology and conditions, completely identical to those used in the example with n-butanol, based on 1.5 g of the steroid and 15 cm3n-propanol. Thus obtained 0.55 g of crude desired product, which is purified in ethyl ether, as in the previous example. Get 0,353 g of pure product. As before, combine the fallopian water and Dov is ucaut 0,650 g of the target product or the output is of 53.7 %.

Various uterine water, obtained above, again combined and concentrated to dryness. Dissolve 0,78 g of the obtained crude product in THF and determine the titer of the target product by HPLC. So get 0,177 g of pure product, identical to the product of example 1 of the application.

The total balance of the reaction is therefore 0,712 g, which corresponds to a yield of 58.6 %.

Example 8. 17-Oxepin-4-ene-3,11,20-Trion.

Stage A. 9-Chloro - 11,17-dioxopregna-4-ene-3,20-dione.

Mix in the atmosphere of inert gas 2 g 17-oxepin of 4.9/11/-diene-3,20-dione and 10 cm3of tetrahydrofuran, then added at 0oC 1 g N-chlorosuccinimide. Cooled to -3oC, then slowly add the mixture of 1.3 cm365% perchloric acid and 2.5 cm3water. Stirred for 3.5 hours, then poured into 100 cm3a mixture of ice-water. Filter the crystals, washed with water and dried. Obtain 2.3 g of the target product, used as such for the next stage.

Stage Century. 17-Oxepin-4-ene-3,11,20-Trion.

Work as described for stage b of example 1, using of 2.06 g of 9-chloro - 11,17-dioxopregna-4-ene-3,20-dione and obtain 1.2 g of the desired product after chromatography of the crude product oxide kremegne-3,11,20- -trione.

Stage A. 9-Bromo - 11,17-dihydroxy-21-acetoxyphenyl-3,20 - dione.

Mix in the atmosphere of inert gas of 4.7 g of 17-hydroxy-21- -acetamiprid-9(11)-ene-3,20-dione and 65 cm3of tetrahydrofuran, and then at a temperature of 0o/-5oC enter 3,26 g of N - bromosuccinimide. Slowly add the mixture of 2.6 cm370% perchloric acid and 5.2 cm3water. After stirring for 1 hour at a temperature of 0oC/5oC, pour a solution of 50 volume mixture of ice water, filtered, the crystals washed and dried. Obtain 5.9 g of the target product used in the next stage.

Stage Century. 17-Hydroxy-21-acetoxyphenyl-3,11,20-Trion.

Bring to the boil under reflux in an atmosphere of inert gas, a mixture of 0.7 g of the compound obtained in stage A, 5 cm3ethyl acetate and 1.6 cm3of ethylene glycol. Maintained at the reflux for 5 hours, then cooled to 20oC and add 1.1 cm3of concentrated hydrochloric acid and 13 cm3water. Stirred for 16 hours, and ethyl acetate is distilled off under reduced pressure. Saturated with sodium chloride, then centrifuged obtained crystals are washed with water, saturated sodium chloride, dried and recrystallized from acetone. Poluchaeti formula I

< / BR>
where R is hydrogen or acyl WITH1- C8;

R1is methyl, radical, CH2OR11where R11is hydrogen or acyl WITH1- C8, 3-oxoprop can be protected in the form of

< / BR>
where n = 2;

- possible double bond,

by conversion of compounds of General formula II

< / BR>
where R, R1have the specified values,

in gelegenheden General formula III

< / BR>
where X is bromine or chlorine;

R, R1have the specified values,

characterized in that gelegenheden General formula III is subjected to a rearrangement reaction in the presence of an alcohol to obtain after treatment with acid target compounds of General formula I.

2. The method according to p. 1, wherein the rearrangement reaction is carried out in the presence of a higher alcohol or a polyhydric alcohol taken in excess.

3. The method according to PP. 1 and 2, characterized in that the rearrangement reaction is carried out in the presence of ethylene glycol.

4. The method according to p. 1, wherein the rearrangement reaction is carried out at a heating at a temperature below 100oC.

5. The method according to PP. 1 to 4, characterized in that the rearrangement reaction is carried out at a heating at a temperature below 100oC.

oWith the reflux.

7. The method according to p. 6, wherein the co-solvent is ethyl acetate.

 

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< / BR>
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< / BR>
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EFFECT: improved preparing method, valuable medicinal properties of compounds.

11 cl, 1 tbl, 9 ex

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