Methods of obtaining 2-perfluoroalkyl-3-oxazoline-5-she, the intermediate

 

(57) Abstract:

Describes the method of obtaining 2-perfluoroalkyl-3-oxazoline-5 - she of the formula (II) where n = 1-8, integer, R is the Deputy of the formulas (a) and (b), where L is hydrogen or halogen, M and Q each independently is hydrogen, halogen or1-C4-haloalkyl; R1, R2and R3is hydrogen; W - S, on the basis of aminonitriles, characterized in that it comprises the reaction of aminonitriles formula III, where R has the above significance, with perforations agent of the formula IV, where n has the values, m is 1 or 2, X - OR1, Cl or O, and R1is hydrogen or C1-C6-alkyl, provided that when X is O, m = 2, and when X is Cl or or1then m = 1, in the presence of a solvent and optionally in the presence of a base to produce an intermediate product performanceenhancing formula (I), where R and n have the specified values. The described method allows to obtain new compounds that are effective means against insects, mites and nematodes. Also describes these new compounds of formula (I) suitable for use upon receipt, 2-TRANS-foralkyl-3-oxazoline-5-it. 3 S. and 4 C.p. f-crystals, 2 PL.

< / BR>
< / BR>
< / BR>
< / BR>

Connection Ari is ESA and nematodes. In particular, it was found that the compounds 2-aryl-5-cryptomaterial-3-carbonitrile and their derivatives have a broad spectrum of activity at very low application rates with efficacy against resistant species. U.S. patent 5030735 describes the methods of preparation of these compounds of the pyrrole in an industrial scale and includes 1,3-dipolar cycloaddition of the corresponding 3-oxazoline-5-one with 2-chloroacrylonitrile. Before that, get the key intermediate 3-oxazoline-5-it is through the corresponding connection phenylglycine in the cycle of the synthesis of 4 steps, which starts with the previous aminonitriles.

The purpose of this invention is to provide an efficient method for the synthesis of 2-perfluoroalkyl-3-oxazoline-5-it in two stages from aminonitriles predecessor.

In addition, the purpose of this invention is to provide compounds of performanceoriented suitable for use in obtaining 2-perfluoroalkyl-3-oxazoline-5-it.

Another circuit of this invention is to provide a convenient source of key intermediate product in the production of compounds arylpyrol for combating insects, mites and nematodes.

Proposed method 1 - 8;

R is

< / BR>
or

< / BR>
L is hydrogen or halogen;

M and Q are each independently hydrogen or halogen;

CN, NO2WITH1-C4alkyl, C1-C4haloalkyl,1-C4alkoxy, C1-C4haloalkoxy,1-C4alkylthio,1-C4alkylsulfonyl or when M and Q are in adjacent positions, they may together with the carbon atoms to which they are attached, form a ring in which MQ represents the structure

-OCH2O-, -OCF2O - or-CH=CH-CH=CH-

with the proviso that at least one of L, M and Q must be something other than hydrogen; R1, R2and R3are, each independently, hydrogen, halogen, NO2CHO, or R2and R3may together with the atoms to which they are attached, form a ring in which R2R3represented by the structure

< / BR>
R2, R5, R6and R7are each, independently, hydrogen, halogen, CN or NO2;

W is O or S,

which involves the reaction of aminonitriles formula III

< / BR>
where R is as described above, with perforations agent of the formula IV

< / BR>
where m = 1 or 2, X is a OR11then m = 1, in the presence of a solvent, optionally in the presence of a base, to obtain an intermediate product of performanceoriented formula I.

< / BR>
and the cyclization of the intermediate product of formula I in the presence of acid and at least one molar equivalent of water.

It is also envisaged intermediate product performanceoriented formula I.

< / BR>
where n is an integer of 1 to 8;

R is

< / BR>
or

< / BR>
L is hydrogen or halogen;

M and Q are each independently, hydrogen, halogen,

CN, NO2WITH1-C4-alkyl, C1-C4-haloalkyl,1-C4-alkoxy, C1-C4-haloalkoxy,

WITH1-C4-alkylthio,1-C4-alkylsulfonyl or when M and Q are in adjacent positions, they may together with the carbon atoms to which they are attached, form a ring in which MQ represents the structure

-OCH2O-, -OCF2O - or-CH=CH-CH=CH-

with the proviso that at least one of L, M and Q is different from hydrogen;

R1, R2and R3are, each independently, hydrogen, halogen, NO2CHO, or R2 represented by the structure

< / BR>
R4, R5, R6and R7are, each independently, hydrogen, halogen, CN or NO2and

W is O or S,

Connection 2-perfluoroalkyl-3-oxazoline-5-it is a key intermediate product in the production of pyrrole compounds for combating insects, mites and nematodes.

Connection arylpyrol, in particular, the compounds of the 2-aryl-5 - cryptomaterial-3-carbonitrile, are a new class of highly effective tools for combating insects, mites and nematodes. The key intermediate product in obtaining them is the connection of 2-perfluoroalkyl-3-oxazoline-5-it formula

< / BR>
where n and R are as described above. Currently known methods of obtaining oxazolinone formula II include obtaining the corresponding compounds arigliano V by hydrolysis of aminonitriles III. Aminonitriles produced by the Strecker synthesis from the corresponding aldehydo predecessor (W. L. Matier et al J. Med. Chem., 1973, 16, 901). Protection of the amino group in aminonitriles III by acetylation to VI, followed by acid hydrolysis as ceanography and protective groups due to the instability of aminonitriles III in terms of g is oxazoline II in 4 stages. The sequence of reactions shown in scheme 1, where R is chlorophenyl, and n = 1

Now found that the direct perforazione product of the Strecker synthesis III gives an intermediate product performanceoriented 1, which can be easily converted to the desired 2-perfluoroalkyl-3-oxazoline-5-about the connection II. The reaction shown in the scheme II, where m = 1 or 2, X is Cl, OR1or O, and R1is hydrogen or C1-C6- alkyl, provided that when X is O, then m = 2, and when X is Cl or or1then m = 1.

Suddenly, performanceoriented formula 1 can be cycletour in one stage, with a good yield in the conditions of the aqueous acid solution, the compound 2-perfluoroalkyl-3-oxazoline-5-it formula II.

Mainly desired oxazoline can be obtained in 2 stages of product aminonitriles III Strecker.

Preferred compounds of formula I are those in which n = 1, 2 or 3, more preferred those in which n = 1. Also preferred are those compounds of formula I in which R is phenyl, optionally substituted by halogen atoms, one to three, NO2C1-C4-haloalkyl or1-

Solvents suitable for use in the method of this invention are aromatic hydrocarbons or halogenated aromatic hydrocarbons, preferably aromatic hydrocarbons such as toluene, benzene, xylene and the like, more preferably, toluene.

Acids suitable for use in the method of this invention include sulfuric acid, methanesulfonate acid, p-toluensulfonate acid, naphtalenesulfonic acid, fluorine-boric acid, nortryptaline complexes and the like. Nortryptaline complexes may include BF3Ateret, BF3methanol complex, BF3ethanol complex, BF3the dihydrate and the like. Water can be represented in the form of a hydrate, i.e. monohydrate p-toluensulfonate acid, or with the dissolved substance, such as 30-60% ethylchloride, used as a reagent of the formula IV can be added equimolar amount of the base as the HCl absorber. Among the bases which can be used, carbonates or bicarbonates of alkali metals, or mixtures thereof, or tertiary amines. Carbonates of alkali metals such as sodium carbonate or potassium carbonate can also be considered as bicarbonates, such as sodium bicarbonate or potassium.

Tertiary amines suitable for use in the method of this invention include any trehzameshchenny Amin, known from the literature, such as trialkylamine, dialkylanilines, triarylamine and the like, preferably, trialkylamine, more preferably triethylamine.

For a clearer understanding of the invention, the following examples. These examples are only illustrative and should not be construed as limiting the scope or underlying principles of the invention in any way.

The term 1H,13C and19F NMR indicate nuclear magnetic resonance of the proton, carbon-13 and fluorine 19, respectively.

Example 1. Obtaining N-[(p-Chlorobenzyl)cyanomethyl]-2,2,2 - trifurcated

< / BR>
< / BR>
Method A: Paramesh Is, 1.5 mol) at 35oC during 90-minute period. The mixture is treated with heptane, and the resulting precipitate is filtered and the filtered cake was washed with toluene/ heptane, getting listed in title product, 323,7 g, yield 82%, so pl. 127-128oC defined using the1H,13C and19F NMR analyses.

Method B: a Solution of CYANOGEN chlorobenzylamino (83,3 g, 0.5 mol) in methanol is treated with ethyltryptamine (to 85.2 g, 0.6 mol), stirred at room temperature for about 16 hours and was concentrated in vacuo, receiving the remainder. The residue is crystallized from toluene/heptane, getting listed in title product as a pale yellow solid product, of 88.3 g, yield 67.2 per cent, so pl. 127-128oC.

Method C: a Mixture of CYANOGEN chlorobenzylamino (83,3 g, 0.5 mol) and triethylamine (50.6 g, 0.5 mol) in toluene is treated dropwise with triftoratsetilatsetonom (66,2 g, 0.5 mol), stirred at ambient temperature for about 1 hour and filtered. The filtrate is washed once with water and concentrated in vacuo, receiving sediment. The residue is crystallized in toluene/hexane, getting listed in title product, 114,2 g, yield 87%, so pl. 127-128oC.

Example 2. Obtaining N-(Killermetal)-2,2,2-triflora is lsua appropriate - canbeseen, as the source material, you receive the following for N-(Killermetal)-2,2,2-trifurcation products. Products determined using analysis1H,13C and19F NMR.

Example 3. Obtaining N - Cantieni)-2,2,2-trifurcated

< / BR>
Using basically the same procedure described as method A in example 1, and using the original product Strecker, - cyan-2-thiophenemethylamine, as source material, get listed in the title of the product with the release ofand) 23%, so pl. 73,0-74,5oC, is determined using the1H,13C and19F NMR analysis.

(a) In relation to the original aldehyde used in the Strecker synthesis.

Example 4. Obtaining N-[( Chlorophenyl)lanmeter]-2,2,3,3,4,4,4 - getattributenames

< / BR>
Using basically the same procedure described as method A of example 1, and using heptaprenyl anhydride as perforaciones agent, get listed in title product in the form of white crystals with a yield of 95%, so pl. 93,0-95,0oC, is determined using the1H,13C and19F NMR analyses.

Example 5. Obtaining N-[( Chlorophenyl)lanmeter]-2,2,3,3,3 - pentafluoropropane

< / BR>
Using mainly solid fuel perforaciones agent, get listed in title product as white crystals, yield 95%, so pl. 118,0-118,5oC, is determined using the1H,13C and19F NMR analyses.

Example 6. Getting 4-( Chlorophenyl-2-(trifluoromethyl)-3 - oxazoline-5-it

< / BR>
Method A: a Solution of N-[ Chlorophenyl)lanmeter]-2,2,2 - trifurcated (0.1 mol) in toluene at 80oC handle, parts, monohydrate toluensulfonate acid ( tsa H2O) (0.11 mol) over 0,75-1,0-hour period, stirred at 90-95oC for 2-3 hours, cooled and filtered. The filtrate is washed twice with water and concentrated in vacuo, obtaining an oily residue. The oil is dissolved in heptane, filtered and the filtrate distil under vacuum, getting listed in title product in the form of oil, the yield of 55.6%, because 78oC/0.01 mm Hg, determined using1H,13C and19F NMR analyses.

Method B: a Solution of N-( chlorophenyl)lanmeter - 2,2,2-trifurcated (26,3 g, 0.1 mol) in toluene and in methanesulfonic acid (10.7 g, 0.11 mol) at 80oC is treated with water (2 ml, 0.11 mol) over a 20 minute period, stirred at 90oC for 8 hours and cooled. The reaction mixture is washed twice with water. The organic layer was concentrated in vacuo, receiving mA the m Hg.

Example 7. Getting 4-(2-Thienyl-2-(trifluoromethyl)-3-oxazoline-5-it

< / BR>
Using basically the same procedure described as method A of example 6 and using N-( - )cantieni)- 2,2,2-triptorelin as source material, get listed in title product as a pale brown solid, yield 50%, so pl. 62,0-65,0oC, determined using IR and1H,13C and19F NMR analyses.

Example 8. Getting 2-perfluoroalkyl-3-oxazoline-5-it

< / BR>
Using basically the same procedure described as method A of example 6, and using the appropriate performanceoriented as source material, get connections, presented in table II. ).

1. The method of obtaining 2-perfluoroalkyl-3-oxazoline-5-she formulas II

< / BR>
where n = 1 - 8, integer;

R is

< / BR>
where L is hydrogen or halogen; M and Q each independently is hydrogen, halogen or C1- C4-haloalkyl; R1- R3is hydrogen; W is S,

based aminonitriles, characterized in that it comprises the reaction of aminonitriles formula III

< / BR>
where R has the above meaning,

with perforations agent of the formula IV

< / BR>
where n has the value what about when X is O, m = 2, and when X is Cl or or1then m = 1,

in the presence of a solvent and optionally in the presence of a base to produce an intermediate product performanceoriented formula I

< / BR>
where R and n have the specified values,

and the cyclization of the intermediate product of formula I in the presence of acid, and at least 1 mol of water.

2. The method according to p. 1, where perforations agent of the formula IV is

< / BR>
or

< / BR>
3. The method according to p. 2, where perforations agent is

< / BR>
and there is the base, and the base is sodium carbonate or potassium, or tertiary amine.

4. The method according to p. 1, where the solvent is an aromatic hydrocarbon or halogenated aromatic hydrocarbon and the acid is sulfuric acid, methanesulfonic acid, benzosulfimide acid, p-toluensulfonate acid, naphtalenesulfonic acid, forborne acid or nortryptaline complex.

5. The method of obtaining 2-perfluoroalkyl-3-oxazoline-5-she formulas II

< / BR>
where n and R are as defined in paragraph 1,

which involves the cyclization of the compounds of formula I

< / BR>
in the presence of acid and at mariashoni acid, p-toluensulfonate acid, naphtalenesulfonic acid, forborne acid or nortryptaline complex.

7. Performanceoriented formula I

< / BR>
where n = 1 - 8, integer;

R is

< / BR>
where L is hydrogen or halogen;

M and Q each independently is hydrogen, halogen or C1- C4-haloalkyl;

R1- R3is hydrogen;

W - S.

 

Same patents:

The invention relates to a derivative of oxazolidinone

The invention relates to the field of organic chemistry, specifically to a method for producing 2-(furyl-2)-1,3-oxazolidine formula I

< / BR>
with astragalina activity

The invention relates to certain condensed to errorcorrection that selectively associated with GABA receptors

The invention relates to agriculture and can be used to accelerate growth and increase crop yields

The invention relates to derivatives of 5-aryl-isoxazol of, compositions containing them, methods for their preparation and their use as herbicides

FIELD: organic synthesis.

SUBSTANCE: invention provides compounds of general formula I:

, where R1 represents -CO-Ra, -SO2-Rb, or aryl optionally substituted by lower alkoxy, wherein Ra represents cycloalkyl, cycloalkyl(lower)alkyl, cycloalkyloxy, aryl, aryloxy, aryl(lower)alkyl, aryl(lower)alkoxy, aryloxy(lower)alkyl, aryl-S-(lower)alkyl, aryl(lower)alkenyl, provided that aryl group can be optionally substituted by halogen, lower alkyl, hydroxy, nitro, cyano, lower alkoxy, phenyl, CF3, cyano(lower)alkyl, lower alkyl-C(O)NH, lower alkyl-CO, and lower alkyl-S; heteroaryl, heteroaryl(lower)alkyl, or heteroaryl(lower)alkoxy, provided that heteroaryl group is 5- or 6-membered ring or bicyclic aromatic group constituted by two 5- or 6-membered rings including 1-3 heteroatoms selected from oxygen, nitrogen, and sulfur and that heteroaryl group can be optionally substituted by lower alkoxy; Rb represents aryl, aryl(lower)alkyl, or heteroaryl, aryl group optionally substituted by halogen, cyano, or lower alkyl-C(O)NH; R2 and R3 represent hydrogen atoms; R4 representshydrogen or lower alkyl; R5 represents hydrogen, lower alkyl, cycloalkyl, benzodioxyl, or aryl optionally substituted by lower alkyl, halogen, lower alkoxy, hydroxy, or (lower)alkyl-C(O)O; n is 1 or 2; and pharmaceutically acceptable salts thereof and/or pharmaceutically acceptable esters thereof. Invention also provides a pharmaceutical composition exhibiting inhibitory activity with regard to cysteine proteases of the cathepsin family, which composition comprises compound of formula I, pharmaceutically acceptable recipient, and/or adjuvant.

EFFECT: increased choice of cysteine protease inhibitors.

34 cl, 1 tbl, 13 ex

FIELD: organic chemistry, medicine, biochemistry, pharmacy.

SUBSTANCE: invention relates to compound of the formula (I) wherein R1 means hydrogen atom, (C1-C6)-alkyl or hydroxy-(C1-C6)-alkyl; R2 means -CO-NR8R9, -(CH2)n-NR8R9, -(CH2)p-OR8 or -(CH2)n-CN; R3 is chosen from hydrogen atom, halogen atom, halogen-(C1-C6)-alkyl; R4, R6 and R7 mean hydrogen atom, fluorine atom and, as minimally, one radical of R4, R5, R6 and R7 means fluorine atom; R8 and R9 mean independently of one another hydrogen atom or (C1-C6)-alkyl; m means 1, 2 or 3; n means 0, 1, 2 or 3; p means 1 or 2, and to their pharmaceutically acceptable salts. Also, invention relates to a medicinal agent possessing inhibitory effect with respect to activity of monoaminoxidase B and comprising one or some compounds of the formula (I) as an active component and pharmaceutically acceptable excipients. Invention proposes derivatives of fluorobenzamide possessing inhibitory effect with respect to activity of monoaminoxidase B.

EFFECT: valuable medicinal and biochemical properties of compounds and pharmaceutical composition.

27 cl, 60 ex

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of formula I, where R stands for halo-С16alkyl, Х1 stands for halogen, and Х1, if m is more than 1, may stand for various halogen atoms, Х2 stands for halogen, and Х2, if n is more than 1, may stand for various halogen atoms, m is 1 or 2 and n is 1, 2 or 3, which can be used for warm-blood animal pest (nematodes, mites or insects) control. Invention also relates to therapeutic composition and pest control method.

EFFECT: provides for preparation of pharmaceutical composition of direct action against warm-blood animal pests.

7 cl, 2 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: method involves 1) dividing a racemate into two pure enantiomers via chromatographic separation on a chiral polysaccharide as a stationary phase with alcohol as the mobile phase and sorption of the eutomer, 2) repeated racemisation of the distomer with a base using a catalyst in a solvent selected from ether or a mixture of solvents containing ether, at temperature between 80°C and 120°C and 3) subjecting the obtained racemate to separation at step 1) in a repeated cycle. The invention also pertains to use of a pure S-enantiomeric form of a formula I compound, particularly (-)-(S)-N-(1-cyano-2-(5-cyano-2-trifluoromethylphenoxy)-1-methylethyl)-4-trifluoromethylsulfanylbenzamide, for control of entozoic parasites of warm-blooded animals, such as helminths.

EFFECT: efficient method of producing a unique enantiomer from a racemate of amidoacetonitrile compound having a formula in which R1, R2 and R3 independently denote cyano, halo-C1-C6alkyl or halo-C1-C6alkylthio.

15 cl, 1 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: present invention refers to new compounds of formula I or their pharmaceutically acceptable salts showing an ability to inhibit sphingosine kinase, to a based pharmaceutical composition, to a method of inhibiting sphingosine kinase and a method of treating diseases specified in breast cancer, diabetic retinopathy, arthritis and colitis. , wherein X represents -C(R3,R4)N(R5)-, -C(O)N(R4)-; R1 represents phenyl unsubstituted or substituted by 1 or 2 halogens. The values of R2, R3, R4, R5 substitutes are such as specified in the patent claim.

EFFECT: preparation of new compounds.

17 cl, 24 dwg, 9 tbl, 26 ex

FIELD: chemistry, pharmacology.

SUBSTANCE: claimed invention relates to agonist of receptor of glucagone-like peptide-1, which can be applied for treatment of diseases, caused by disturbance of glycometabolism, such as type II diabetes, insensibility to insulin or obesity. In structural formula each of Ar1 and Ar2 independently represents substituted phenyl, and group-substituents represent one, two or three groups selected from C1-C6alkoxyl, C1-C6-alkanoylamino, which is substituted with hydroxyl (which contains groups-substituents, including hydroxyl); C3-C6-cyclolkanoylamino, C2-C6-lkenoylamino; banzoylamino, banzyloxy C1-C6-alkanoylamino, thenoyloxy, tret-butoxyformamido, adamantanformamido; and mandeloylamino; X represents O; Y represents O. Invention also relates to method of obtaining agonist, and to its application for obtaining medication for treatment of diseases caused by disturbance of glycometabolism.

EFFECT: obtaining medication for treatment of diseases caused by disturbance of glycometabolism.

8 cl, 4 ex, 2 tbl, 2 dwg

FIELD: medicine.

SUBSTANCE: invention is related to compound of formula (I), (values of radicals are described in formula of invention) or its pharmaceutically acceptable salts, to methods of its production, pharmaceutical composition, which contains it. Application of invention is described for manufacturing of medicinal agent intended for provision of inhibiting action in respect to HDAC in warm-blooded animal, in production of agent used for treatment of malignant tumor. Method is also described for provision of inhibiting action in warm-blooded animal.

EFFECT: compounds have inhibiting activity in respect to HDAC.

15 cl, 17 tbl, 24 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: present invention refers to compounds of formula Ia and their pharmaceutically acceptable salts, hydrates, solvates, esters and amides. In formula Ia , A is specified from -C(O)OR5 where R5 represents hydrogen; W represents C1-3alkylene; Y is specified from phenyl and 5-6-member heteroaryl containing one heteroatom specified from N, S, O; where any phenyl or heteroaryl Y can be optionally substituted with 1 to 3 radicals specified from halogen, C1-6alkyl, C1-6alkoxygroup, halogen-substituted C1-6alkyl and halogen-substituted C1-6alkoxygroup; Z is specified from: where left and right asterisks Z specify an attachment point between -C(R3)(R4)- and A of formula la; R6 is specified from hydrogen and C1-6alkyl; or R6 can be attached to carbon atom in Y to form a 5-7-member ring; R1 is specified from phenyl and 5-member heteroaryl containing one heteroatom specified from S, O; where any phenyl or heteroaryl R1 is substituted with a radical specified from phenylC0-4alkyl, heteroarylC0-4alkyl where heteroaryl represents 5-6-member heteroary containing one heteroatom specified from N, S, O, C3-8cycloalkylC0-4alkyl, C3-8heterocycloalkylC0-4alkyl which contains nitrogen atom as heteroatom, or C1-6alkyl; where any phenyl, heteroaryl, cycloalkyl or heterocycloalkyl group R1 can be optionally substituted with 1 to 3 radicals specified from halogen, C1-6alkyl, C1-6alkoxygroup, halogen-substituted C1-6alkyl group and halogen-substituted C1-6alkoxygroup; R2 represents C1-6alkyl group; R3 and R4 represent hydrogen.

EFFECT: preparation of the pharmaceutical composition exhibiting EDG/S1P receptor modulating properties, containing therapeutically effective amount of the compound under the invention, development of a method of treating the disease mediated by EDG/S1P receptor activity, application of the compounds for preparing a drug for prevention or treatment of the disease mediated by EDG/S1P receptor activity.

16 cl, 1 tbl, 86 ex

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of formulae (1) and (2), where R1 is H or alkyl with 1-6 carbon atoms, R2 is H, alkyl with 1-6 carbon atoms or R1 and R2 together with a nitrogen atom form a saturated or unsaturated 5-, 6- or 7-member ring which can also include one or two heteroatoms independently selected from N, O or S. Said 5-, 6- or 7-member ring is possibly substituted with one or two OH groups or halogen groups, and said 5-, 6- or 7-member ring is possibly condensed with an aromatic or non-aromatic 5- or 6-member ring; R3 is independently selected from H, alkyl with 1-20 carbon atoms, cycloalkyl with 3-6 carbon atoms, phenyl or phenyl-alkyl, where the alkyl group has 1-4 carbon atoms, phenyl(hydroxy)alkyl, where the alkyl group has 1-4 carbon atoms, wherein said phenyl groups are possibly substituted with 1-3 groups independently selected from a group comprising halogen, alkyl with 1-6 carbon atoms, alkoxy with 1-6 carbon atoms, or R3 is CO-R7 or CO-O-R7, where R7 is H, alkyl with 1-20 carbon atoms, optionally substituted with a NH2 group or NH-CO alkyl group, where the alkyl group has 1-6 carbon atoms, phenyl or phenyl-alkyl, where the alkyl group has 1-4 carbon atoms, wherein said phenyl groups are possibly substituted with 1-3 groups independently selected from a group comprising halogen, alkyl with 1-6 carbon atoms, alkoxy with 1-6 carbon atoms, is H, alkyl with 1-6 carbon atoms or CO-R8, where R8 is alkyl with 1-6 carbon atoms; wavy lines denote bonds with carbon atoms, having an R or S configuration; dotted lines denote a bond or absence of a bond provided that the ring containing dotted lines is aromatic; m, n and q are whole numbers independently selected from 0, 1, 2 or 3, provided that the sum of m, n and q equals 2 or 3; s equals 0 or 1; W, X and Y independently denote CH, CR5, CR6 or a heteroatom independently selected from N, O and S, and R5 and R6 are independently selected from H, halogen, alkyl with 1-6 carbon atoms, halogen-substituted alkyl with 1-6 carbon atoms, alkoxy with 1-6 carbon atoms and thioxy with 1-3 carbon atoms, phenyl, or R5 and R6 together with atoms to which they are bonded form a carbocyclic ring which has 6 atoms in the ring, or a heterocyclic ring which has 5 or 6 atoms in the ring and 1-3 heteroatoms independently selected from N, O and S. Said carbocyclic or heterocyclic ring, formed jointly by R5 and R6, is possibly substituted with 1-6 R9 groups, where R9 is a halogen.

EFFECT: higher pain-killing and immune-stimulating action.

65 cl, 1 tbl, 256 ex

Up!