CH617184A5 - Process for the preparation of bis-O-sulphamylglycols and bis-O-sulphamylglycols thus prepared - Google Patents

Description

The present invention relates to a process for the preparation of bis-O-sulfamylglycols of the general formula (I)

<jH2 ° S02NRlR2

(CXY)

In

I.

CH20S02NR1R2

in which n has the value 0 or an integer in the range from 1 to 8, _

X and Y represent hydrogen atoms and, if n has the value 1, X and Y represent hydrogen atoms or lower alkyl radicals, aryl, aralkyl or cyclohexyl radicals, and

R 1 and R 2 are independently hydrogen atoms or alkyl, aryl, aralkyl or cycloalkyl radicals, or

Ri and R2 together with the nitrogen atom to which they are attached form a pyrrolidinyl ring or piperidinyl ring.

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617 184

The compounds of the formula (I) are suitable for regulating the fertility of male animals because they influence the sperm and thus cause so-called functional sterility of the male animals.

Compounds with sulfamoyl groups have already been described in the literature. Thus, US Pat. No. 2,889,562 describes aryl aminosulfonic acid esters, and US Pat. No. 3,898,262 describes substituted 0- (aminosulfonyl) glycolic acid anilides which have herbicidal properties.

Also in US Pat. No. 3,383,195 compounds with herbicidal activity are described which are m- (3,3-dimethylureido) -phenyldimethylcarbamate. In all of the publications mentioned, only those compounds are described which have a single sulfamoyl group in their molecule.

US Pat. No. 3,082,238 describes aryl dialkyl sulfamates in which 1 or 2 groups of the formula -0-SO2-N (R) 2 are bonded to an aromatic nucleus, and these compounds can be used as herbicides or fungicides will. With regard to their chemical structure, they differ from the compounds of the formula (I) to be prepared by the process according to the invention in that phenolic hydroxyl groups and not hydroxyl groups of a glycol are esterified with the sulfamoyl group.

U.S. Patent No. 2,862,919 describes disazo dyes in which each of two phenolic hydroxyl groups is esterified with an arylsulfonic acid which has an azo group in its aryl nucleus as a substituent.

Finally, in U.S. Patent No. 3,927,090 there are compounds of the following structure

CH3 ^ 02-CX2-S02NR1R2

explained in which both a sulfamoyl group and also a methylsulfonyl group and also the radicals X in the meaning of chlorine atoms or bromine atoms are bonded to a single carbon atom. The compounds described there also differ in their action from the compounds of the formula (I) to be prepared by the process according to the invention in that they have anti-microbial activity.

The process according to the invention for the preparation of the bis-o-sulfamyl glycols of the formula (I) is characterized in that either a) for the preparation of compounds of the general formula (I), a glycol of the formula (II)

ch0 - oh

I.

(CXY) II

I D

ch2 - oh which one

X, Y and n have the same meanings as in formula (I),

with a sulfamyl halide of the formula (III)

(Hal) -S02NR! R2 (III)

in which

Rj and R2 have the meaning given in formula (I), and

Shark represents a halogen atom,

in a solvent in the presence of a strong base, or b) to prepare compounds of the general formula (ia) ch2oso2nh2

(Ia)

(cxy)

n ch2oso2nh2

in which

X, Y and n have the meaning given in formula (I),

the glycol of the general formula (II) with a sulfamoyl halide of the formula (purple) which has a protective group

RNHS02 (HaI) (purple)

in which

R is a protecting group and

Shark means a halogen atom,

reacted in a solvent in the presence of a strong base and the product obtained was treated with an acid to remove the protective group.

If, according to process variant b), the compounds of the formula (I) in which all the radicals Ra and R2 have the meaning of hydrogen atoms are prepared, the protective group is preferably cleaved off using a strong acid.

If in the end products of the formula (I) the radicals X and Y have the meaning of lower alkyl radicals, then these preferably have 1 to 3 carbon atoms, and preferred meanings for the radicals X and Y in the meaning of aryl and aralkyl groups are phenyl radicals, Benzyl residues and phenethyl groups.

Preferred meanings for the radicals R 1 and R 2 are alkyl radicals having 1 to 7 carbon atoms, phenyl radicals, benzyl radicals, phenethyl radicals, phenylpropyl groups, cyclopentyl and cyclohexyl groups. However, it is particularly preferred if the radicals R 1 and R 2 are hydrogen atoms. Accordingly, glycols of the formula (II) which are preferably used are 1,2-ethanediol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol and 1,10-decanediol.

Specific examples of sulfamyl halides of the general formula (III) which can be used in the process according to the invention are sulfamyl chloride and correspondingly N-mono- or N, N-disubstituted sulfamyl halides. As strong bases come e.g. B. sodium hydride, sodium amide, sodium hydroxide, pyridine and tributyltin in question. Specific examples of solvents that can be used are 1,2-dimethoxyethane, diethyl ether, tetrahydrofuran, diethylene glycol dimethyl ether and p-dioxane. The reaction with the sulfamyl halide can be carried out at room temperature. However, it is preferably carried out at temperatures from 0 to 10 ° C. The sulfamate is isolated by customary methods.

In alternative method b) for the preparation of the aliphatic primary sulfamates of the general formula (Ia) come as glycols, for. B. 1,2-ethanediol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol and 1,10-decanediol in question. A sulfamyl halide substituted by a protective group is used as the sulfamyl halide of the general formula (purple). This protective group must be removable by an acid, preferably a strong acid. Specific examples of the protective group are the tert-butyl and benzyl group, α-alkylbenzyl, allyl and 1-alkylallyl radicals, the alkyl radicals containing 1 to 3 carbon atoms.

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Specific examples of strong acids by means of which the protective group can be split off are trifluoroacetic acid, trichloroacetic acid, methanesulfonic acid, concentrated sulfuric acid and concentrated hydrochloric acid.

The production of unsubstituted sulfamyl halides is inherently dangerous. These dangers are avoided by using substituted sulfamyl halides. The substituted sulfamyl halides can be prepared by reacting an amine such as tert-butylamine or benzylamine with a sulfuryl halide in a solvent such as acetonitrile in the presence of a strong base. Specific examples of strong bases that are used for the start reaction are sodium hydride, potassium tert-butoxide, potassium hydride, tributyltin, sodium amide and sodium hydroxide. As a solvent such. B. toluene, benzene, xylene, diethyl ether, tetrahydrofuran, diethylene glycol dimethyl ether, 1,2-dimethoxyethane and p-dioxane in question.

The reaction of the substituted sulfamyl halides can be carried out at room temperature; However, temperatures of 15 to 60 ° C. are preferred. The protecting groups are preferably cleaved at room temperature under a protective gas such as nitrogen.

The invention further relates to the bis-O-sulfamyl glycols of the formula (I) prepared by the process according to the invention.

As already mentioned, the bis-O-sulfamyl glycols of the formula (I) prepared by the process according to the invention can be used to regulate the fertility of male animals. They influence the sperm in the epididymids and cause so-called functional sterility. The gametes show no morphological changes and maintain their motility, but normal fertilization is no longer achieved.

Amounts of 5 to 200 mg of the compounds of formula (I) per kilogram of body weight are effective to bring about functional sterility, the preferred dosages being 10 to 150 mg per kilogram of body weight.

In addition to this effect, the compounds of the formula (I) prepared by the process according to the invention also have antiandrogenic properties. This is shown by an inhibition of the growth of the ventral prostate.

The effect of compounds which inhibit the fertility of male animals by changing the functional capacity of the sperm in the epididymids is generally determined as follows:

The compounds are administered to the animals for 2 weeks. This corresponds to the time required for the sperm to migrate through the epididymids. This results in a separation of the compounds which influence the maturation of the sperm in the epididymids and / or their function, from the antispermiogenic compounds which lead to sterility with a longer delay.

Each test was carried out on five male rats with a body weight of 250 to 300 g. They were kept in temperature-controlled cages and provided with laboratory food and tap water as desired. The compounds to be tested were dissolved or suspended in carriers (usually methyl cellulose) and administered daily for 14 consecutive days (i.g.). Control animals received only the vehicle. After the 14-day treatment, each male rat was individually caged to a female rat in the oestrus state. The following morning, vaginal swabs from the female rats were examined to check for mating. If no mating occurred, the male rat in question was again added to a female rat in the Proestrus state the following night. The male rats were sacrificed and autopsied the following day, and a rough examination of the tests, epididymids, and accessory sexual organs was performed. Tissue samples from these organs were taken for histological examination if the autopsy suggested that the test compounds had an effect. Regardless of whether sperm was found during vaginal douching, the female rats were autopsied 14 days after cohabitation and examined for pregnancy.

The inability of female rats to develop a viable embryo after successful mating with a treated male rat is a measure of functional infertility. The number of male rats mated with female rats that mated with them is a measure of the influence of the compound on libido. The largest of the accessory sexual organs provides an indication of the effect on androgen formation. Microscopic examination of the epididymid sperm gives information about the quality (motility and morphology) and quantity of the sperm.

The examples illustrate the invention.

example 1

1,2-bis-0-sulfamyl-1,2-ethanediol A solution of 3.1 g (0.05 mol) of ethylene glycol in 100 ml of 1,2-dimethoxyethane is mixed with a 57% dispersion of 8.45 g ( 0.20 mol) sodium hydride added to mineral oil. The suspension obtained is stirred for 2 hours at room temperature and then cooled to 4 ° C. Then 20.79 g (0.18 mol) of sulfamyl chloride are dissolved in 400 ml of 1,2-dimethoxyethane and added dropwise to the suspension with stirring. The reaction mixture is stirred at 4 ° C. for a further 24 hours. A solid precipitates, which is filtered off. The filtrate is concentrated. The residue is shaken between heptane and methanol. The methanol phase is then concentrated to a syrup, which is digested with ethyl acetate and brought to crystallization. Yield 6.1 g (58% of theory) of the title compound, mp 96.5 to 99 ° C.

If 1,5-pentanediol is used in the process according to Example 1, 1,5-bis-0-sulfamyl-1,5-pentadiol is obtained.

Example 2 1, 10-bis-0-sulfamyl-1, 10-decanediol A solution of 8.71 g (0.05 mol) of 1,10-decanediol in 100 ml of 1,2-dimethoxyethane is mixed with a 57% dispersion 8.45 g (0.20 mol) of sodium hydride in mineral oil. The suspension obtained is stirred for 2 hours at room temperature and then cooled to 4 ° C. Then 20.79 g (0.18 mol) of sulfamyl chloride are dissolved in 400 ml of 1,2-dimethoxyethane and added dropwise to the suspension with stirring. The reaction mixture is stirred at 4 ° C. for a further 48 hours. A solid precipitates, which is filtered off. The filtrate is concentrated. The residue is shaken between heptane and methanol. The methanol phase is then concentrated to a syrup, which is digested with ethyl acetate and brought to crystallization. Yield 6.0 g (36% of theory) of the title compound, mp. 129 to 131 ° C.

When 1,6-hexanediol is used in the process according to Example 2, 1,6-bis-0-sulfamyl-1,6-hexanediol is obtained.

Example 3

1,4-bis-O-sulfamyl-1,4-butanediol A solution of 4.5 g (0.05 mol) of 1,4-butanediol in 100 ml of 1,2-dimethoxyethane is mixed with a 57% dispersion of 8 , 45 g (0.20 mol) of sodium hydride in mineral oil. The solution obtained is stirred for 2 hours at room temperature and then cooled to 4 ° C. Then

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20.79 g (0.18 mol) of sulfamyl chloride are dissolved in 400 ml of 1,2-dimethoxyethane and added dropwise to the suspension with stirring. The reaction mixture is stirred at 4 ° C. for a further 48 hours. A solid precipitates, which is filtered off. The filtrate is concentrated. The residue is shaken between heptane and methanol. The methanol phase is then concentrated to a syrup, which is digested with ethanol and brought to crystallization. Yield 5.5 g (47% of theory) of the title compound, mp 126 to 129 ° C.

If 1,7-heptanediol is used in the process according to Example 3, 1,7-bis-0-sulfamyl-1,7-heptanediol is obtained.

Example 4 1,3-bis-O-sulfamyl-1,3-propanediol A solution of 11.41 g (0.15 mol) of 1,3-propanediol in 100 ml of 1,2-dimethoxyethane is mixed with a 57% dispersion of 25.4 g (0.60 mol) of sodium hydride in mineral oil. The suspension obtained is stirred for 12 hours at room temperature and then cooled to 4 ° C. Then 62.37 g (0.54 mol) of sulfamyl chloride are dissolved in'400 ml of 1,2-dimethoxyethane and added dropwise to the suspension with stirring. The reaction mixture is stirred at 4 ° C. for a further 24 hours. A solid precipitates, which is filtered off. The filtrate is concentrated. The residue is shaken between heptane and methanol. The methanol phase is then concentrated to a syrup. The residue is washed with heptane and chromatographed on a column filled with SilicAR CC-7 using a mixture of acetone and chloroform (1: 1) as the eluent. The fractions are combined and the solvent is evaporated off. The title compound remains as a crystalline residue, mp. 85 to 87.5 ° C.

When using 1,8-octanediol or 1,9-nonanediol in the process according to Example 4, 1,8-bis-O-sulfamyl-1,8-octanediol or 1,9-bis-0-sulfamyl-l, Obtained 9-nonandiol.

Example 5

2-methyl ~ 2-propyl-l, 3-bis-0-sulfamyl-l, 3-propanediol A solution of 10 g (0.076 mol) of 2-methyl-2-propyl-1,3-propanediol in 200 ml of dimethoxyethane is used with a 57% dispersion of 12.7 g (0.3 mol) of sodium hydride in mineral oil and then mixed with a further 400 ml of dimethoxyethane. The suspension obtained is stirred for 18 hours and then cooled to 4 ° C. A solution of 31.2 g (0.27 mol) of sulfamyl chloride in 600 ml of dimethoxyethane is then added dropwise. The suspension obtained is stirred at room temperature for 18 hours. A solid precipitates, which is filtered off. The filtrate is concentrated. The residue is washed with heptane and chromatographed on a column filled with SilicAR CC-7 using a mixture of acetone and chloroform (1: 3) as the eluent. The eluate is evaporated and the residue is recrystallized from a mixture of ethyl acetate, hexane and methylene chloride. The title compound of mp 92 to 94 ° C. is obtained.

When using 2-ethyl-2-propyl-l, 3-propanediol,

2,2-dimethyl-1,3-propanediol or 2-methyl-1,3-propanediol in the process according to Example 5 is 2-ethyl-2-propyl-1,3-bis-0-sulfamyl-1,3-propanediol, 2,2-dimethyl-l, 3-bis-0-sulfamyl

1.3-propanediol or 2-methyl-1,3-to-0-sulfamyl-1,3-propanediol obtained.

Example 6

2,2-Diphenyl-1,3-bis-0-sulfamyl-1,3-propanediol A solution of 17.3 g (0.076 mol) of 2,2-diphenyl-1,3-propanediol in 200 ml of dimethoxyethane is mixed with a 57% dispersion of 12.7 g (0.3 mol) of sodium hydride in mineral oil and then mixed with a further 400 ml of dimethoxyethane. The suspension obtained is stirred for 18 hours and then cooled to 4 ° C. A solution of 31.2 g (0.27 mol) of sulfamyl chloride in 600 ml of dimethoxyethane is then added dropwise. The suspension is stirred at room temperature for 18 hours. A solid precipitates, which is filtered off. The filtrate is concentrated. The residue is washed with heptane and chromatographed on a column filled with SilicAR CC87. The eluate is evaporated and the residue is recrystallized. The title link remains.

When using 2,2-dibenzyl-1,3-propanediol or 2,2-dicyclohexyl-1,3-propanediol in the process according to Example 6, 2,2-dibenzyl-1,3-bis-0-sulfamyl-l , 3-propanediol or 2,2-dicyclohexyl-l, 3-to-0-sulfamyl-l, 3-propanediol.

Example 7

1,2-bis-0- (N, N-dimethylsulfamyl) -1,2-ethanediol

A solution of 3.1 g (0.05 mol) of ethylene glycol in 100 ml of 1,2-dimethoxyethane is mixed with a 57% dispersion of 8.45 g (0.20 mol) of sodium hydride in mineral oil. The suspension obtained is stirred for 2 hours at room temperature and then cooled to 4 ° C. Then 25.8 g (0.18 mol) of N, N-dimethylsulfamyl chloride are dissolved in 400 ml of 1,2-dimethoxyethane and added dropwise to the suspension with stirring. The reaction mixture is stirred at 4 ° C. for a further 24 hours. A solid precipitates, which is filtered off. The filtrate is concentrated. The residue is shaken between heptane and methanol. The methanol phase is then concentrated to a syrup, which is mixed with ethyl acetate. The title compound crystallizes out.

When using N, N-diphenylsulfamyl chloride or N-ethylsulfamyl chloride in the process according to Example 7, 1,2-bis-0- (N, N-diphenylsulfamyl) -l, 2-ethanediol or 1,2-bis-0- Obtained (N-ethylsulfamyl) -l, 2-ethanediol.

When using N-cyclohexylsulfamyl chloride, N, N-dicyclopentylsulfamyl chloride, N, N-dibenzylsulfamylchloride, 1-piperidylsulfonylchloride or 1-pyrrolidinylsulfamyl chloride in the process according to Example 7, 1,2-bis-0- (N-cy- clohexylsulfamyl) -l, 2-ethanediol, l, 2-bis-0- (N, N-dicyclopen-tylsulfamyl) -l, 2-ethanediol, l, 2-bis-0- (N, N-dibenzylsulfamyl) -l, 2-äthandiol, l, 2-bis- (l-piperidylsulfonyl) -l, 2-äthan-diol or l, 2-bis- (l-pyrrolidinylsulfonyl) -l, 2-äthandiol obtained.

Example 8

1,2-bis-O-sulfamyl-1,2-ethane diol

21.7 ml (0.385 mol) of ethylene glycol are added dropwise to a suspension of 37 g (50% m.o., 0.77 mol) of sodium hydride in 450 ml of toluene within 15 minutes. The suspension is stirred for 15 minutes, slowly warmed to 45 to 50 ° C. and stirred at this temperature for a further 2 hours. The reaction mixture is then cooled to 20 ° C., and a solution of 132 g (0.77 mol) of tert-butylsulfamyl chloride in 131 ml of toluene is added dropwise at 1 to 4 hours at 20 to 35 ° C. During this addition, the suspension foams up a lot and cooling is required to keep the temperature at 20 to 35 ° C. The yellow-brown viscous suspension obtained is stirred 2x / 2 hours at 20 ° C, then 1V2 hours at 45 to 50 ° C and finally 16 hours without further heating. A gelatin-like solid is obtained, which is filtered off, washed with toluene and then extracted twice with hot chloroform (600 ml, 300 ml). The remaining dye is suspended in 500 ml of water and extracted with chloroform until no solid remains. The chloroform extracts are combined and evaporated. The solid residue obtained is recrystallized from a mixture of chloroform and heptane. Yield 72.26 g (56.4% of theory) 1,2-bis-O- (N-tert-butylsulfamyl) -l, 2-ethanediol, mp 119 to 121 ° C.

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110 g (0.33 mol) of the crystalline compound obtained are introduced into 330 ml of trifluoroacetic acid at 25 ° C. with stirring and under nitrogen as a protective gas. A clear solution is obtained which is stirred at room temperature for 20 hours. A solid precipitates, which is filtered off, washed with chloroform (2 × 50 ml) and dried at 50 to 55 ° C. under reduced pressure. 61.1 g (84% of theory) of crude product remain. The crude product is dissolved in 185 ml of acetone, heated under reflux and treated with 1.2 g of activated carbon. The activated carbon suspension is refluxed for 5 minutes and then filtered through diatomaceous earth. The colorless filtrate is treated with 185 ml of chloroform, cooled and stirred at 0 to 5 ° C for 1 hour. A solid precipitates, which is filtered off and dried at 50 to 55 ° C. under reduced pressure. Yield 54.0 g (75.5% of theory) of the title compound, mp 98.5 to 101 ° C.

Example 9 1,10-bis-O-sulfamyl-1,10-decanediol According to Example 8, but using 67 g (0.385 mol) of 1,10-decanediol, the title compound is obtained.

If 1,6-hexanediol is used in the process according to Example 9, 1,6-bis-0-sulfamyl-1,6-hexanediol is obtained.

Example 10

1,4-bis-0-sulfamyl-1,4-butanediol According to Example 8, but using 34.6 g (0.385 mol) of 1,4-butanediol, the title compound is obtained.

When using 1,7-heptanediol in the process according to Example 10, 1,7-bis-0-sulfamyl-1,7-heptanediol is obtained.

Example 11 1,3-bis-O-sulfamyl-1,3-propanediol According to Example 8, but using 29.2 g (0.385 mol) of 1,3-propanediol, the title compound is obtained.

When using 1,8-octanediol or 1,9-nonanediol in the process according to Example 11, 1,8-bis-O-sulfamyl-1,8-octanediol or l, 9-bis-0-sulfamyl-l, Obtained 9-nonandiol.

Example 12

2-methyl-2-propyl-1,3-bis-O-sulfamyl-1,3-propanediol According to Example 8, but using 50.8 g (0.385 mol) of 2-methyl-l-propyl-1,3 propanediol, the Ti-5 telverbindung is obtained.

When using 2-ethyI-2-propyI-l, 3-propanediol,

2,2-dimethyl-1,3-propanediol or 2-methyl-1,3-propanediol in the process according to Example 12 is 2-ethyl-2-propyl

1,3-bis-O-sulfamyl-1,3-propanediol, 2,2-dimethyl-1,3-bis-O-10 sulfamyl-1,3-propanediol or 2-methyl-1,3-bis- 0-sulfamyl

Obtained 1,3-propanediol.

Example 13

2,2-Diphenyl-l, 3-to-0-suIfamyI-l, 3-propandioI. As in Example 8, but using 87.7 g (0.385 mol) of 2,2-diphenyl-1,3-propanediol, the title compound is obtained.

When using 2,2-dibenzyl-1,3-propanediol or 2,2-dicyclohexyl-1,3-propanediol in the process according to example 20, 2,2-dibenzyl-1,3-bis-0- Obtained sulfamyl-1,3-propanediol or 2,2-dicyclohexyl-1,3-bis-0-sulfamyl-1,3-propanediol.

Example 14 (preparation of starting material) 25 Preparation of tert-butylsulfamyl chloride

A solution of 240 ml (3 mol) of sulfuryl chloride in 450 ml of acetonitrile is mixed with 65.7 g (0.90 mol) of tert-butylamine within 1 hour at 20 to 30 ° C. There is a strong evolution of hydrogen chloride and the amine-hy-30 hydrochloride separates out as a solid. The mixture is heated under reflux for 24 hours and a further 240 ml of sulfuryl chloride are added. The mixture is then stirred for a further 40 hours and heated under reflux. This creates a solution. The solution is evaporated under reduced pressure 35 to a viscous oil. The oil is distilled under reduced pressure. The main fraction boils at 89 to 94 ° C / 0.3 to 0.5 Torr. Yield 100.1 g (64.8% of theory) of the title compound in translucent, acicular crystals of mp 28 to 30 ° C.

s

Claims (9)

617 184 2. The method according to claim 1, characterized in that in process b) the reaction is carried out in the presence of sodium hydride as a strong base. 2nd PATENT CLAIMS 1. Process for the preparation of bis-O-sulfamylglycols of the general formula (I) CH2oso2Nrlr2 (CXY) n I. CH20S02NR] lR2 in which n has the value 0 or an integer in the range from 1 to 8, X and Y represent hydrogen atoms and, if n has the value 1, X and Y represent hydrogen atoms or lower alkyl radicals, aryl, aralkyl or cyclohexyl radicals, and R 1 and R 2 independently of one another are hydrogen atoms or alkyl, aryl, aralkyl or or mean cycloalkyl radicals, or Ri and R2 together with the nitrogen atom to which they are attached form a pyrrolidinyl ring or piperidynyl ring, characterized in that either a) for the preparation of compounds of the general formula (I), a glycol of the formula (II) ch0 - oh I. (cxy) ii I n ch2 - oh which one X, Y and n have the same meanings as in formula (I), with a sulfamyl halide of the formula (III) (Hal) -S02NR1R2 (III) in which Ri and R2 have the meaning given in formula (I) and Shark represents a halogen atom, reacted in a solvent in the presence of a strong base, or b) for the preparation of compounds of the general formula (Ia) ch20s02nh2 (Ia) (cxy) n CH2oso2NH2 in which X, Y and n have the meaning given in formula (I), the glycol of the general formula (II) with a sulfamoyl halide of the formula (purple) which has a protective group RNHS02 (Hal) (purple) in which R is a protecting group and Shark means a halogen atom, reacted in a solvent in the presence of a strong base and the product obtained was treated with an acid to remove the protective group. 3. The method according to claim 1, characterized in that in process b) the protective group is split off with a strong acid, in particular with trifluoroacetic acid. 4. The method according to claim 1, characterized in that compounds of the formula (I) are prepared in which n is the number 1 and the radicals X and Y are alkyl radicals having 1 to 3 carbon atoms, phenyl radicals, benzyl radicals and phenethyl radicals have. 5. The method according to claim 1, characterized in that compounds of formula (I) are prepared in which the radicals Rj and R2 are alkyl radicals having 1 to 7 carbon atoms, phenyl radicals, benzyl radicals, phenylethyl radicals, phenylpropyl radicals, cyclopentyl radicals or cyclohexyl radicals. 6. The method according to claim 1, characterized in that the glycol of the formula (II) 1,2-ethanediol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol or 1,10-de-candiol used. 7. The method according to claim 1, characterized in that 1,2-dimethoxyethane, diethyl ether, tetrahydrofuran, di-ethylene glycol dimethyl ether or p-dioxane are used as solvents in the reaction. 8. The method according to claim 1, characterized in that one uses in process b) as a protected sulfamoyl halide of the formula (purple), in which the protective group is a tert-butyl group, a benzyl group, an allyl group, a 1-alkylallyl group with 1 to 3 carbon atoms in the alkyl radical. or is an a-alkyl-benzyl group having 1 to 3 carbon atoms in the alkyl group. 9. Bis-O-sulfamyl glycols of the formula (I) prepared by the process according to claim 1.