Derivatives benzoperylene containing their medicines and pharmaceutical composition

 

(57) Abstract:

The invention relates to organic chemistry, namely to new derivatives of benzoperylene. Describes derivatives of benzoperylene General formula (I),

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where the radicals R1, R2, R3and R4such as presented in paragraph 1 of the claims. As described pharmaceutical composition based on compounds of the formula (I), the amplifier lipid metabolism, an inhibitor of the biosynthesis of triglycerides, the agent reducing triglycerides in the blood, the agent that increases the content of HDL, the agent for the prevention of atherosclerosis and agent for treatment of atherosclerosis. The technical result obtained new compounds with useful biological properties. 8 c. and 24 C.p. f-crystals, 3 tables.

The present invention relates to new derivatives of benzofuran--Piron and medicines containing these derivatives as active ingredients. More specifically, the invention relates to new derivatives of benzofuran--Piron and amplifiers (enhancers) of lipid metabolism, agents for the prevention of atherosclerosis, agents for the treatment of atherosclerosis, inhibitors of the biosynthesis of triglycerides, agents, reduce the content of TRIG these derivatives as active ingredients.

Art

Contained in blood cholesterol and triglycerides (TG), in General, by themselves, do not dissolve in the blood and are in the form of lipoproteins by binding with apolipoproteins. In the body of the biosynthesis of triglycerides initially occurs in the liver from acetyl-COA, which is derived from sugars, as an initial matter, and so on, using 6 different enzymes and one group of enzymes (acetyl-COA carboxylase, group synthase fatty acid synthetase fatty acyl-COA, acyltransferase glycerophosphoric acid, acyltransferase lysophosphatidic acid phosphatase, fosfatidov acid and acyltransferase diacylglycerol), and they are secreted from the liver into the blood as lipoproteins.

A condition in which the level of cholesterol and/or triglycerides in the blood are higher than normal, known as hyperlipidemia. The state called hyperlipidemia, are divided into 6 types, depending on the type of lipoproteins in the blood in accordance with the classification of Fredrickson (Fredrikson) (WHO classification). Types I, IV and V are characterized by increased content of only triglycerides, type IIA - increase cholesterol and types IIb and III content increases and that, and the other is (which reduce the content of cholesterol or reduce the content of cholesterol, and triglycerides) are not always suitable for use in all types of hyperlipidemia. In particular, among male patients with hyperlipidemia, there are 40 to 50% of cases of hyperlipidemia type IV ("Rinsho to Kenkyu", 69, 318 (1992)). Most forms of hyperlipidemia in secondary symptoms that accompany diabetes, also belong to type IV ("Sogo Rinsho", 43, 878 (1994)).

Hypertriglyceridemia is a condition in which increased levels of triglycerides in the blood, and in the last few years, she attracts the attention of doctors, clinicians and manufacturers of pharmaceutical products as a risk factor in the development of atherosclerosis and coronary heart disease.

As hyperlipidemia including hypertriglyceridemia, attention mostly concentrated on one cholesterol directly involved in the development of atherosclerosis, we developed few medicines to reduce the content of triglycerides, and treatment of hypertriglyceridemia was limited to the use of lipid-lowering drugs on the basis of clofibrate (clofibrate) or structures on the basis of nicotinic acid as existing lipid-lowering drugs. As t concern a number of related side effects of The Lipid, 5, 65 to 72 (1994)). Therefore, it would be highly desirable to find a new type of medicines, which has the effect of reducing the amount of triglycerides in low doses, does not cause side effects and has a specific mechanism of action.

Hypertriglyceridemia occurs as a result of different factors, including genetic background and, as mentioned above, the secondary symptoms that accompany diabetes and so on ("Sogo Rinsho", 43, 878 (1994); more specifically, its causes include:

A. strengthening of synthesis (secretion) of triglycerides in the liver, and

C. delay the decomposition of the synthesized triglycerides (present in the blood as lipoproteins) with the participation of lipoprotein lipase (LPL) ("Rinsho to Kenkyu", 69, 340 (1992)). In particular, in the case of hypertriglyceridemia associated with diabetes, the GA is considered to be a cause of insulin-dependent diabetes mellitus (NIDDM), while the Century is considered to be a cause of insulin-dependent diabetes mellitus (IDDM) ("Rinsho to Kenkyu", 69, 379 (1992)). Thus, it is believed that the mechanism of action of therapeutic agents for the treatment of hypertriglyceridemia is the synthesis inhibition (secretion) of triglycerides in the liver and/or enhanced decomposition of the synthesized triglycerides (present in blood is the local derivative of a-pyrone with Deputy heteroaromatic ring in position 6, see for example, WO 9635664, WO 9514013, WO 9514014, EP 588137, US 4668803, FR 2665445, Japanese laid out an application SHO 49-5976, Japanese laid claim 8-503216, Japanese laid claim 9-505291, Japanese laid claim 9-505293, Japanese laid claim 9-505294, Japanese laid claim 9-505295, or, for example. Tetrahedron Letters, 37, 6461 (1996), J. Chem. Research (S), 86 (1994), Chem. Pharm. Bull., 32, 1665 (1984), Chem. Ber., 100, 658 (1967) and J. Org. Chem., 54, 3985 (1989).

However, in the prior art was not published any explanations or assumptions concerning the effect of inhibition of the biosynthesis of triglycerides, the effect of reducing triglycerides in the blood, or the effect of increasing content of HDL in the blood, manifesting any of these derivatives-pyrone.

Among the publications of the prior art, WO 9635664 and EP 588137 describes the connection of such a structure, in which phenyl is a substituent in the C-3 position of the ring-pyrone, but not described and not assume the use of the alkyl group instead of a phenyl group as the substituent at C-3 position of the ring-pyrone.

Similarly, among the publications of the prior art in US 4668803 described derivatives-pyrone in which the substituent in the C-3 position is an acyl group containing from 2 desto acyl group, containing from 2 to 11 carbon atoms, or phenyl group as the substituent at C-3 position of the ring-pyrone.

Among the publications of the prior art in FR 2665445 described derivatives-pyrone in which the substituent at C-4 position is a group-S(O)n-R1where n is 1 or 2 and R1represents an alkyl group containing from 1 to 6 carbon atoms, benzyl group or phenyl group. However, not described and not supposed to use IT, OCOR or OSO2R groups instead of-S(O))n-R1as the substituents in the C-4 position of the ring-pyrone.

Similarly, among the publications of the prior art in Japanese application laid 49-5976 described derivatives-pyrone with hydrogen, a lower alkyl group or phenyl as a substituent in the C-4 position, but not described and not supposed to use IT, OCOR or OSO2R groups instead of hydrogen, a lower alkyl group or phenyl as substituents at C-4 position of the ring-pyrone.

Similarly, among the publications of the prior art in hem. Ber., 100, 658 (1967) described derivatives-pyrone with hydrogen, stands or ethyl as a substituent in the C-4 position,as substituents at C-4 position of the ring-pyrone.

Similarly, among the publications of the prior art in J. Chem. Research (S), 86 (1994) described derivatives-pyrone with SMe group as the substituent at C-4 position, but not described and not supposed to use IT, OCOR or OS02R groups instead SMe group as the substituent at C-4 position of the ring-pyrone.

In addition, among the publications of the prior art in Tetrahedron Letters, 37, 6461 (1996), Chem. Pharm. Bull., 32, 1665 (1984) and J. Org. Chem., 54, 3985 (1989) described derivatives-pyrone with peredelnoj group as the substituent at C-6 position, but not described and not supposed to use benzoperylene group instead peredelnoj group as the substituent at C-6 position of the ring-pyrone.

The invention

The present invention is to provide derivatives of benzofuran--Piron and, in particular, the new derivatives benzofuran--pyrone containing benzofuranol group as the substituent at C-6 position of the ring-pyrone.

Another object of the invention is the provision of amplifiers (enhancers) of lipid metabolism, agents for the prevention of atherosclerosis, agents for the treatment of atherosclerosis and, in particular, ensuring inhibitors biosante the blood, containing as active ingredient new derivatives of benzofuran--pyrone containing benzofuranol group as the substituent at C-6 position of the ring-pyrone.

There have been numerous studies in light of the above prior art, and in the result it was found that the derivative benzofuran--Piron and especially derivatives benzofuran--pyrone containing benzofuranol group as the substituent at C-6 position of the ring-pyrone have the effect of inhibition of the biosynthesis of triglycerides, the effect of reducing the amount of triglycerides in the blood and the effect of increasing the content of HDL in the blood; the present invention has achieved more in-depth research in this area.

Specifically, the present invention provides deriving benzofuran--Piron (and their salts) represented by the following structural formula (I)

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where R1represents a hydrogen or alkyl group containing from 1 to 5 carbon atoms;

R2represents hydrogen, -CO-R5(where R5represents hydrogen, alkyl group containing from 1 to 5 carbon atoms, optionally containing substituents, cycloalkylation) or-SO2R6(where R6represents an alkyl group containing from 1 to 5 carbon atoms, optionally substituted with halogen, or aryl group containing from 6 to 10 carbon atoms);

R3represents hydrogen, alkyl group containing from 1 to 5 carbon atoms, alkenylphenol group containing from 2 to 5 carbon atoms, alkylamino group containing from 2 to 5 carbon atoms, cycloalkyl group containing from 3 to 7 carbon atoms, cycloalkyl group containing from 3 to 7 carbon atoms alkyl group containing from 1 to 5 carbon atoms, aryl group containing from 6 to 10 carbon atoms, aracelio group containing from 7 to 20 carbon atoms, an alkoxy group, containing from 1 to 5 carbon atoms, or aryloxy group containing from 6 to 10 carbon atoms;

R4is a substituent at C-4 position, 5-position, 6-position or the C-7 position benzofuranol ring and represents:

R4Athat represents hydrogen, nitro group, cyano group, halogen atom, a heterocycle, alkenylphenol group containing from 2 to 5 carbon atoms, alkylamino group containing from 2 to 5 carbon atoms, aryl group containing from 6 to 10 atomo is a double bond and n is 0, 1 or 2), A=CH(CH2)mO- (where a represents the alicyclic heterocycle, "=" represents a double bond and m is 1, 2 or 3), A-SO2(CH2)m- (where a represents a heterocycle alicyclic and m represents 1, 2 or 3), -OR7(where R7represents hydrogen, cycloalkyl group containing from 3 to 7 carbon atoms, aryl group containing from 6 to 10 carbon atoms, a heterocycle, alkylsulfonyl group containing from 1 to 4 carbon atoms, optionally substituted with halogen, or arylsulfonyl group containing from 6 to 10 carbon atoms), -O-CO-R8(where R8represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, aryl group containing from 6 to 10 carbon atoms, aracelio group containing from 1 to 20 carbon atoms, or a heterocycle), -NR9R10(where each of R9and R10independently represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, aracelio group containing from 7 to 20 carbon atoms, a phenyl group, a heterocycle, -SO2-R11(where R11represents optionally substituted with halogen alkyl group containing from 1 to 12 at the, containing from 6 to 10 carbon atoms, a heterocycle or aracelio group containing from 7 to 20 carbon atoms) or-CO-R12(where R12represents hydrogen, alkyl group containing from 1 to 12 carbon atoms, aryl group containing from 6 to 10 carbon atoms, aracelio group containing from 7 to 20 carbon atoms, a heterocycle, an alkoxy group containing from 1 to 10 carbon atoms, substituted heterocycle alkyl group containing from 1 to 6 carbon atoms, aryloxy group containing from 6 to 10 carbon atoms, heteroaromatic group or aralkylated group containing from 7 to 20 carbon atoms)), -CO-R13(where R13represents hydrogen, -HE, the alkyl group containing from 1 to 4 carbon atoms, aryl group containing from 6 to 10 carbon atoms, a heterocycle, an alkoxy group containing from 1 to 4 carbon atoms, aryloxy group containing from 6 to 10 carbon atoms, or aralkylated group containing from 7 to 20 carbon atoms), or-CO-NR14R15(where each of R14and R15independently represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, cycloalkyl group containing from 3 to 7 carbon atoms, aryl group containing from 6 Aolcom alkyl group, containing from 1 to 4 carbon atoms);

R4bthat represents a saturated or unsaturated alkoxy group containing from 1 to 6 carbon atoms, optionally substituted by 1-3 groups selected from the group consisting of halogen, cycloalkyl groups containing from 3 to 7 carbon atoms, phenyl, naphthyl, heterocycle, -OR16(where R16represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, phenyl group, naftalina group, benzyl group, or a heterocycle), -O-CO-R16(where R16represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, phenyl group, naftalina group, benzyl group, or a heterocycle), -NR17R18(where each of R17and R18independently represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, a heterocycle, alkylsulfonyl group containing from 1 to 4 carbon atoms, phenylsulfonyl group, -SO2-Het where Het represents a heterocycle), aminosulfonyl group, methylaminomethyl group, dimethylaminomethyl group, diethylaminomethyl group or alkyl group containing from 1 to 4 atmosukarto substituted one is droxia, -NH-CO-R19(where R19represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, phenyl group, naftalina group, a benzyl group, a heterocycle, an alkoxy group containing from 1 to 4 carbon atoms, or benzyloxy group), -CO-R20(where R20represents hydrogen, heterocycle, alkoxy group containing from 1 to 4 carbon atoms, phenoxy group, benzyloxy group or-OR21(where R21represents hydrogen or a heterocycle), and-CO-NR22R23(where each of R22and R23independently represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, benzyl group or a heterocycle); or

R4cthat represents an alkyl group containing from 1 to 4 carbon atoms, optionally substituted by 1-3 groups selected from the group consisting of halogen, cycloalkyl groups containing from 3 to 7 carbon atoms, phenyl, naphthyl, heterocycle, -SH, -OR16(where R16represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, phenyl group, naftalina group, benzyl group, or a heterocycle), -O-CO-R16(where R16represents hydrogen, alkyl group, SUP>18(where each of R17and R18independently represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, a heterocycle, alkylsulfonyl group containing from 1 to 4 carbon atoms, phenylsulfonyl group, -SO2-Het where Het represents a heterocycle), aminosulfonyl group, methylaminomethyl group, dimethylaminomethyl group, diethylaminomethyl group or alkyl group containing from 1 to 4 carbon atoms, substituted by one or two groups selected from phenyl, heterocyclic compounds, phenoxy, O-Het where Het represents a heterocycle), and hydroxyl), -NH-CO-R19(where R19represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, phenyl group, naftalina group, a benzyl group, a heterocycle, an alkoxy group containing from 1 to 4 carbon atoms, or benzyloxy group), -CO-R20(where R20represents hydrogen, heterocycle, alkoxy group containing from 1 to 4 carbon atoms/ phenoxy group, benzyloxy group or-OR21(where R21represents hydrogen or a heterocycle), and-CO-NR22R23(where each of R22and R23independently represents hydrogen, alkyl GRU is, denote position in benzofuranol the ring.

The present invention also provides pharmaceutical compositions comprising a therapeutically effective dose of the derivatives benzofuran--Piron represented by the above structural formula (I) or their salts with pharmaceutically acceptable carriers.

The invention, furthermore, provides amplifiers (enhancers) of lipid metabolism, inhibitors of the biosynthesis of triglycerides, agents that reduce triglycerides in the blood, agents that increase the amount of HDL in the blood, agents for the prevention of atherosclerosis or agents for the treatment of atherosclerosis comprising as active ingredients derived benzofuran--Piron represented by the above structural formula (I) or their salts.

The implementation of the invention

Here is a definition of terms used in this description alone or in combination with other terms. However, the invention is by no means the case is not limited to the specific examples listed below.

"Alkyl" denotes a linear or branched alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tre the ing group, such as vinyl, 1-propenyl, Isopropenyl, 2-butenyl, 3-butenyl, 1-pentenyl or 2-pentenyl.

"Quinil" denotes a linear or branched alkylamino group, such as ethinyl, 1-PROPYNYL, 2-PROPYNYL, 1-butynyl, 2-butynyl, 3-butynyl, 2-methyl-3-butynyl, 1-pentenyl, 2-pentenyl, 3-pentenyl or 4-pentenyl.

"Cycloalkyl" means cycloalkyl group containing from 3 to 7 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl.

"Cycloalkyl group containing from 3 to 7 carbon atoms is an alkyl group containing from 1 to 5 carbon atoms" is a group comprising the above-mentioned cycloalkyl group containing from 3 to 7 carbon atoms, and alkyl group containing from 1 to 5 carbon atoms, as examples cyclopropylmethyl, cyclopentylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclohexylethyl and cycloheptylmethyl.

"Aryl" means an aromatic ring containing from 6 to 10 carbon atoms, such as phenyl or naphthyl.

"Heterocycle" means a heterocycle containing, as constituent parts of rings from 1 to 4 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, and which is irately, triazolyl, tetrazolyl, pyrrolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, thienyl, oxazolyl or isoxazolyl, or 5 - to 7-membered heteroalicyclic group, such as diazolidinyl, oxazolidinyl, imidazolidinyl, pyrrolidinyl, piperidyl, morpholinyl, piperazinil, homopiperazine, tetrahydrofuryl, tetrahydropyranyl, DIOXOLANYL, dioxane, oxazinyl, triazinyl, diazines or pyrazolidine; it also includes bicyclic group condensed with benzene, cycloalkyl groups containing from 3 to 7 carbon atoms, and other heteroaromatic or heteroalicyclic rings, moreover, heteroaromatic or heteroalicyclic ring may also be optionally substituted and where chemically possible, a nitrogen atom or a sulfur atom may be oxidized form.

"Heteroaryl" refers to heteroaromatic group from among the heterocycles listed above.

"Aralkyl" refers to a group containing 7 to 20 carbon atoms, comprising the above-mentioned alkyl group containing from 1 to 5 carbon atoms, and aryl group containing from 6 to 10 carbon atoms, as examples are benzyl, phenethyl, phenylpropyl will benkou as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy, isopentane, 3-pentyloxy, 2,2-DIMETHYLPROPANE, n-hexyloxy, 4-methylpentylamino or 2-ethylbutane.

"Unsaturated alkoxy" denotes a linear or branched unsaturated alkoxy group, such as vinyloxy, allyloxy, 2-propenyloxy, 2-propenyloxy, 2-methyl-2-propenyloxy, 1 butenyloxy, 2-butenyloxy, 3 butenyloxy, 2-butenyloxy, 2-pentyloxy, 3 hexenoate, 5-hexenoate or 5 hexyloxy.

"Aryloxy" means aryloxy group containing from 6 to 10 carbon atoms, such as phenoxy or naphthyloxy.

"Aralkylated" represents a group comprising the above-mentioned alkoxy group containing from 1 to 5 carbon atoms, and aryl group containing from 6 to 10 carbon atoms, as examples, benzyloxy, penetrate, phenylpropoxy, trityloxy, naphthalenyloxy.

"Cycloalkane" means cycloalkane group containing from 3 to 7 carbon atoms, such as cyclopropane, CYCLOBUTANE, cyclopentyloxy, cyclohexyloxy or Cycloheptane.

"Acyl" denotes a linear or branched acyl group containing or 3,3,3-gameiphone.

"Arylcarbamoyl" means arylcarbamoyl group containing from 7 to 11 carbon atoms, such as benzoyl or afterburner.

"Alkylsulfonyl" means alkylsulfonyl group containing from 1 to 5 carbon atoms, such as methanesulfonyl, econsultancy or n-propanesulfonyl.

"Arylsulfonyl" means arylsulfonyl group containing from 6 to 10 carbon atoms, such as phenylsulfonyl or naphthylmethyl.

Ring of aryl, phenyl, naphthyl and heterocycle may be substituted by 1-4 substituents selected from the group consisting of, for example, HE, carboxyl, cyano, phenyl, heterocycle, -SO2NH2, -SO2H, alkylsulfonyl groups, such as methylsulfonyl, ethylsulfonyl, dimethylsulphamoyl and so on, phenylsulfonyl, benzylcarbamoyl, morpholinoethyl, alkylsulfonyl groups such as methanesulfonyl, econsultancy, n-propanesulfonyl and so on, arylsulfonyl groups such as phenylsulfonyl, naphthalenesulfonyl etc., amino, methylenedioxy, alkoxy groups containing from 1 to 5 carbon atoms, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, n-pentyloxy, and so on, alkylamino, such as metiram is thylamino and so on, acylamino groups, such as formamido, acetylamino, propionamido, n-Butylimino and so on, alkoxycarbonyl groups, such as methoxycarbonylamino, ethoxycarbonyl, n-propoxycarbonyl, n-butoxycarbonylamino, tert-butoxycarbonylamino and so on , arachidonoylethanolamine groups, such as benzyloxycarbonylamino, naphthylethylenediamine and so on, alkylsulfonyl groups, such as methanesulfonamido, ethanolamine, n-propanesulfinamide and so on, arylsulfonyl groups, such as phenylcarbonylamino, naphthalenemethylamine etc., nitro, hydroxymethyl, alkyl groups containing from 1 to 5 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl and so on, kalkilya groups such as benzyl, phenethyl, trityl, naphthylmethyl and so on, aralkylated groups such as benzyloxy, penetrate, phenylpropoxy, trityloxy, naphthalenyloxy and so on, acyl groups such as formyl, acetyl, propionyl, n-butyryl, isobutyryl, n-valeryl, trimethylacetyl, 3,3,3-trimethylpropyl and so on, alkoxycarbonyl groups, such as methoxycarbonyl, etoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, tert-butoxycarbonyl and so on, aryloxy as benzyloxycarbonyl, ventilatsioonil, trisiloxanes, naphthylethylenediamine and so on, carbarnoyl, alkylcarboxylic groups, such as methylcarbamoyl, dimethylcarbamoyl, ethylcarbitol, diethylcarbamoyl, n-propellerblades, n-butylcarbamoyl and so on, halogenated methyl groups, such as chloromethyl, methyl bromide, trifluoromethyl, and so on , and halogen atoms, i.e. fluorine, chlorine, bromine and iodine; when chemically possible, they can be substituted by 1 to 3 oxo groups or thioxo groups.

In the formula (I) above, R1represents a hydrogen or alkyl group containing from 1 to 5 carbon atoms. As alkyl groups containing from 1 to 5 carbon atoms can be given, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl and 3-pentyl.

As preferred groups for R1can be hydrogen, methyl, ethyl and isopropyl, and methyl can be described as especially preferred groups for R1.

In the formula (I) above, R2represents hydrogen, -CO-R5(where R5represents hydrogen, alkyl group containing from 1 to 5 carbon atoms, optional sodot 6 to 10 carbon atoms or a heterocycle), or-SO2R6(where R6represents optionally substituted with halogen alkyl group containing from 1 to 5 carbon atoms, or aryl group containing from 6 to 10 carbon atoms).

When R2represents a-CO-R5and R5the group is an alkyl group containing from 1 to 5 carbon atoms, optionally containing a Deputy, an alkyl group containing from 1 to 5 carbon atoms as R5can represent, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 3-pentyl and so on, among which methyl, ethyl and isopropyl are preferred.

Optional substituents alkyl groups containing from 1 to 5 carbon atoms as R5include all well-known experts in this field substituents alkyl groups, for example, they include halogen atoms, -HE, carboxyl group, formyl group, acyl group, cyano group, nitro group, amino group, mercapto groups, sulphonate groups, aryl groups containing from 6 to 10 carbon atoms, heterocycles, cycloalkyl group containing from 3 to 7 carbon atoms and their protected form; in particular, may be PR is holding from 6 to 10 carbon atoms, aranceles group containing from 7 to 20 carbon atoms, heterocycle, acyl group containing from 1 to 5 carbon atoms, arylcarboxylic group containing from 7 to 11 carbon atoms, or aralkylamines group containing from 8 to 21 carbon atoms; -O-CO-Het where Het represents a heterocycle); cycloalkyl group containing from 3 to 7 carbon atoms; aryl groups containing from 6 to 10 carbon atoms; heterocyclic compounds; amino group; amino group-protected alkyl group, containing from 1 to 4 carbon atoms, aranceles group containing from 7 to 20 carbon atoms, optionally substituted with halogen alkylsulfonyl group containing from 1 to 4 carbon atoms, arylsulfonyl group containing from 6 to 10 carbon atoms, acyl group containing from 1 to 5 carbon atoms, arylcarboxylic group containing from 7 to 11 carbon atoms, aralkylamines group containing from 8 to 21 carbon atoms, alkoxycarbonyl group containing from 2 to 5 carbon atoms, aracelikarsaalyna group containing from 8 to 21 carbon atoms, or heterocycle; -NH-CO-Het where Het represents a heterocycle); acyl groups containing from 1 to 5 carbon atoms; carboxyl hsie from 7 to 11 carbon atoms; aracelikarsaalyna group containing from 8 to 21 carbon atoms; -CO-O-Het where Het represents a heterocycle); carbamoyl group, alkylcarboxylic group containing from 2 to 5 carbon atoms; aralkylamines group containing from 8 to 21 carbon atoms; -CO-NH-Het where Het represents a heterocycle); and-CO-Het where Het represents a heterocycle). As the preferred substituents among these may be mentioned phenyl, aryloxy, amino, tert-butoxycarbonylamino, benzyloxycarbonylamino (benzyloxycarbonylamino)methylamino, acetylamino and morpholinylcarbonyl.

When R2represents-COR5and R5the group is cycloalkyl group containing from 3 to 7 carbon atoms, cycloalkyl group containing from 3 to 7 carbon atoms as R5may be such as, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and so on, among which the cyclohexyl is preferred.

When R2represents-COR5and R5the group is an aryl group containing from 6 to 10 carbon atoms, aryl group containing from 6 to 10 carbon atoms as R5m is When R2represents-COR5and R5the group represents a heterocycle, the heterocycle as R5may be such as, for example, imidazolyl, thiazolyl, isothiazolin, pyrazolyl, triazolyl, pyrrolyl, pyridyl, pyrimidinyl, pyrazinyl, furyl, thienyl, isoxazolyl, diazolidinyl, oxazolidinyl, imidazolidinyl, pyrrolidinyl, piperidyl, morpholinyl, piperazinil, Tetra Hydra furyl, tetrahydropyranyl and so on, among which the pyridyl/ pyrrolidinyl and furyl are preferred.

As preferred groups for R5can be described alkyl groups containing from 1 to 5 carbon atoms, optionally containing substituents, among which may be mentioned methyl, methyl or ethyl, substituted by phenyl, aryloxy, amino, tert-butoxycarbonylamino, benzyloxycarbonylamino, (benzyloxycarbonyl)-N-methylamino, acetylamino or morpholinylcarbonyl, and isopropyl; aryl groups containing from 6 to 10 carbon atoms, among which may be mentioned phenyl; and heterocycles, among which may be mentioned pyridyl, pyrrolidinyl and furyl.

When R2represents-SO2R6and R6the group is an optionally substituted galuppo, containing from 1 to 5 carbon atoms as R6can be, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, chloromethyl, methyl bromide, trifluoromethyl, and so on, among which methyl and trifluoromethyl are preferred.

When R2represents-SO2R6and R6represents an aryl group containing from 6 to 10 carbon atoms, aryl group containing from 6 to 10 carbon atoms as R6can be such, as, for example, phenyl, naphthyl and so on, among which phenyl is preferred.

As preferred groups for R6can be given optionally substituted with halogen alkyl groups containing from 1 to 5 carbon atoms, and particularly preferred groups as R6can be given to methyl and trifluoromethyl.

As preferred groups for R2can be hydrogen, -COR70(where R70represents an alkyl group containing from 1 to 5 carbon atoms, optionally containing a Deputy, aryl group containing from 6 to 10 carbon atoms, or a heterocycle and optionally substituted by halogen and the La2can be hydrogen, -COR71(where R71represents a methyl group, a methyl or ethyl group, substituted phenyl, aryloxy, amino, tert-butoxycarbonylamino, benzyloxycarbonylamino, (benzyloxycarbonyl)-N-methylamino, acetylamino or morpholinylcarbonyl; ISO-propyl group; phenyl group; pyridyloxy group; pyrrolidinyl group; or follow group), methanesulfonyl and trifloromethyl.

In the formula (I) above, R3represents hydrogen, alkyl group containing from 1 to 5 carbon atoms, alkenylphenol group containing from 2 to 5 carbon atoms, alkylamino group containing from 2 to 5 carbon atoms, cycloalkyl group containing from 3 to 7 carbon atoms, cycloalkyl group containing from 3 to 7 carbon atoms, an alkyl group containing from 1 to 5 carbon atoms, aryl group containing from 6 to 10 carbon atoms, aracelio group containing from 7 to 20 carbon atoms, an alkoxy group, containing from 1 to 5 carbon atoms or aryloxy group containing from 6 to 10 carbon atoms.

When R3represents an alkyl group containing from 1 to 5 carbon atoms, an alkyl group, isobutyl, sec-butyl, tert-butyl, n-pentyl and so on, among which methyl, ethyl, isopropyl and n-pentyl are preferred.

When R3represents alkenylphenol group containing from 2 to 5 carbon atoms, Alchemilla group containing from 2 to 5 carbon atoms may be such as vinyl, allyl, 1-propenyl, Isopropenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl and so on, among which 2-butanol is preferred.

When R3represents alkylamino group containing from 2 to 5 carbon atoms, Alchemilla group containing from 2 to 5 carbon atoms may be the same as ethinyl, 2-PROPYNYL, 1-PROPYNYL, Isopropenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl and so on, among which 2-butenyl is preferred.

When R3represents cycloalkyl group containing from 3 to 7 carbon atoms, cycloalkyl group containing from 3 to 7 carbon atoms, may be such as, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and so on, among which the cyclohexyl is preferred.

When R3is cycloalkyl containing from 3 to 7 carbon atoms, an alkyl group containing from 1 Dov, carbon can be such as, for example, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cycloheptylmethyl and so on , among which cyclopentylmethyl is preferred.

When R3represents an aryl group containing from 6 to 10 carbon atoms, aryl group containing from 6 to 10 carbon atoms may be the same as, for example, phenyl, naphthyl and so on, among which phenyl is preferred.

When R3represents aracelio group containing from 7 to 20 carbon atoms, kalkilya group containing from 7 to 20 carbon atoms, may be such as, for example, benzyl, phenethyl, phenylpropyl, benzhydryl, trityl, naphthylmethyl and so on, among which benzyl is preferred.

When R3represents an alkoxy group containing from 1 to 5 carbon atoms, alkoxy group containing from 1 to 5 carbon atoms, may be such as, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy and so on, among which methoxy is preferred.

When R3represents aryloxy group containing from 6 to 10 carbon atoms, aryloxy GRU who's fenocchi is preferred.

As preferred groups for R3can be described alkyl groups containing from 1 to 5 carbon atoms, alkeline group containing from 2 to 5 carbon atoms, cycloalkyl group containing from 3 to 7 carbon atoms, alkyl groups containing from 1 to 5 carbon atoms and kalkilya group containing from 7 to 20 carbon atoms, and particularly preferred groups for R3can be described alkyl groups containing from 1 to 5 carbon atoms, among which methyl, ethyl, isopropyl and n-pentyl are preferred; cycloalkyl group containing from 3 to 7 carbon atoms, alkyl groups containing from 1 to 5 carbon atoms, among which cyclopentylmethyl is preferred; and benzyl.

In the formula (I) above, R4represents the substituent at C-4 position, 5 position. C-6 position or the C-7 position benzofuranol ring and represents:

R4athat represents hydrogen, nitro group, cyano group, halogen atom, a heterocycle, alkenylphenol group containing from 2 to 5 carbon atoms, alkylamino group containing from 2 to 5 carbon atoms, aryl group containing from 6 to 10 carbon atoms is strong communication and n has the value 0, 1 or 2), A=CH(CH2)mO- (where a represents the alicyclic heterocycle, "= " represents a double bond and m is 1, 2 or 3), A-SO2(CH2)m- (where a represents a heterocycle alicyclic and m has the value 1, 2 or 3), -OR7(where R7represents hydrogen, cycloalkyl group containing from 3 to 7 carbon atoms, aryl group containing from 6 to 10 carbon atoms, a heterocycle or optionally substituted with halogen alkylsulfonyl group containing up to 4 carbon atoms, or arylsulfonyl group containing from 6 to 10 carbon atoms), -O-CO-R8(where R8represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, aryl group containing from 6 to 10 carbon atoms, aracelio group containing from 7 to 20 carbon atoms or a heterocycle), -NR9R10(where each of R9and R10independently represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, aracelio group containing from 7 to 20 carbon atoms, a phenyl group, a heterocycle, -SO2-R11(where R11represents optionally substituted with halogen alkyl group containing from 1 to 12 atoms Rasul from 6 to 10 carbon atoms, a heterocycle or aracelio group containing from 7 to 20 carbon atoms) or-CO-R12(where R12represents hydrogen, alkyl group containing from 1 to 12 carbon atoms, aryl group containing from 6 to 10 carbon atoms, aracelio group containing from 7 to 20 carbon atoms, a heterocycle, an alkoxy group containing from 1 to 10 carbon atoms, substituted heterocycle alkyl group containing from 1 to 6 carbon atoms, aryloxy group containing from 6 to 10 carbon atoms, heteroaromatic group or aralkylated group containing from 7 to 20 carbon atoms)), -CO-R13(where R13represents hydrogen, -HE, the alkyl group containing from 1 to 4 carbon atoms, aryl group containing from 6 to 10 carbon atoms, a heterocycle, an alkoxy group containing from 1 to 4 carbon atoms, aryloxy group containing from 6 to 10 carbon atoms or aralkylated group containing from 7 to 20 carbon atoms) or-CO-NR14R15(where each of R14and R15independently represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, cycloalkyl group containing from 3 to 7 carbon atoms, aryl group containing from 6 to 10 carbon atoms, aracelio group is from 1 to 4 carbon atoms);

R4bthat represents a saturated or unsaturated alkoxy group containing from 1 to 6 carbon atoms, optionally substituted with from 1 to 3 groups selected from the group consisting of halogen, cycloalkyl groups containing from 3 to 7 carbon atoms, phenyl, naphthyl, heterocycle, -OR16(where R16represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, phenyl group, naftalina group, benzyl group, or a heterocycle), -O-CO-R16(where R16represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, phenyl group, naftalina group, benzyl group, or a heterocycle), -NR17R18(where each R17and R18independently represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, a heterocycle, alkylsulfonyl group containing from 1 to 4 carbon atoms, phenylsulfonyl group, -SO2-Het where Het represents a heterocycle), aminosulfonyl group, methylaminomethyl group, dimethylaminomethyl group, diethylaminomethyl group, or alkyl group containing from 1 to 4 carbon atoms substituted by 1 or 2 groups selected from phenyl is dstanley a hydrogen, alkyl group containing from 1 to 4 carbon atoms, phenyl group, naftalina group, a benzyl group, a heterocycle, an alkoxy group containing from 1 to 4 carbon atoms or benzyloxy group), -CO-R20(where R20represents hydrogen, heterocycle, alkoxy group,

containing from 1 to 4 carbon atoms, phenoxy group, benzyloxy group or-OR21(where R21represents hydrogen or a heterocycle), and-CO-NR22R23(where each R22and R23independently represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, benzyl group or a heterocycle; or R4cthat represents an alkyl group containing from 1 to 4 carbon atoms, optionally substituted from 1 to 3 groups selected from the group consisting of halogen, cycloalkyl groups containing from 3 to 7 carbon atoms, phenyl, naphthyl, heterocycle, -SH, -OR16(where R16represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, phenyl group, naftalina group, benzyl group, or a heterocycle), -O-CO-R16(where R16represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, phenyl group, raftiline dstanley a hydrogen, alkyl group containing from 1 to 4 carbon atoms, a heterocycle, alkylsulfonyl group containing from 1 to 4 carbon atoms, phenylsulfonyl group, -SO2-Het where Het represents a heterocycle), aminosulfonyl group, methylaminomethyl group, dimethylaminomethyl group, diethylaminomethyl group, or alkyl group containing from 1 to 4 carbon atoms substituted by 1 or 2 groups selected from phenyl, heterocyclic compounds, phenoxy, -O-Het where Het represents a heterocycle), and hydroxyl, -NH-CO-R19(where R19represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, phenyl group, naftalina group, a benzyl group, a heterocycle, an alkoxy group containing from 1 to 4 carbon atoms or benzyloxy group), -CO-R20(where R20represents hydrogen, heterocycle, alkoxy group containing from 1 to 4 carbon atoms, phenoxy group, benzyloxy group or-OR21(where R23represents hydrogen or a heterocycle), and-CO-NR22R23(where each R22and R23independently represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, benzyl group or a heterocycle).

Cogdog; nitro; cyano; halogen atoms such as fluorine, chlorine, bromine and iodine; heterocycles such as imidazoles, thiazoles, isothiazolin, pyrazolyl, triazolyl, pyrrolyl, pyridyl, pyrimidinyl, pyrazinyl, furyl, thienyl, isoxazolyl, diazolidinyl, oxazolidinyl, imidazolidinyl, 6-oxo-4,5-benzo-1,3-oxazin-2-yl, 1-occaisonaly-2-yl, pyrrolidinyl, 2.5-dioxopyrimidine, piperidyl, 2,6-dioxopiperidin, 1-(4-bromobenzoyl)piperidine-4-yl, morpholinyl, piperazinil, 2, 3-dioxopiperazinyl, homopiperazine, tetrahydrofuryl and tetrahydropyranyl; alkeneamine groups such as vinyl, allyl, 1-propenyl, Isopropenyl, 2-butenyl, 3-butenyl, 1-pentenyl and 2-pentenyl; alkyline groups, such as ethinyl, 1-PROPYNYL, 2-PROPYNYL, 1-butynyl, 2-butynyl, 3-butynyl, 2-methyl-3-butynyl, 1-pentenyl, 2-pentenyl, 3-pentenyl and 4-pentenyl; aryl groups such as phenyl and naphthyl; hydroxyl; cycloalkane groups, such as cyclopropylamine, cyclobutylamine, cyclopentyloxy, cyclohexyloxy, Cycloheptane; aryloxy groups, such as phenoxy, naphthyloxy; groups that represent-O-Het where Het represents a heterocycle) such as imidazolinone, thiazolidone, isothiazolinone, pyrazolinone, triazolinone, pyrrolidone, pyridyloxy, pyrimidinone, hydroxy, pyrrolidinyloxy, piperidinyloxy, morpholinoethoxy, piperidinyloxy, tetrahydrofurane, tetrahydropyranyloxy; optionally substituted with halogen, alkylsulfonate groups, such as methanesulfonate, econsultancy, p-propanesulfonate, tripterocalyx; arylsulfonate groups, such as phenylsulfonyl, naphthalenesulfonate; acyloxy groups, such as formyloxy, atomic charges, propionyloxy, butyryloxy, isobutyryloxy, trimethylsilyloxy; arylcarbamoyl groups such as benzoyloxy, naftiliaki; aralkylamines groups, such as phenylacetylene, 2-phenylpropionate, 3 phenylbutyrate, diphenylacetylene, naphthylacetate group that represents-O-CO-Het where Het represents a heterocycle)such as imidazolidinone, thiazolidinone, isothiazolinones, pyrazolylborate, triazolinones, pyrrolidinone, pyridylcarbonyl, pyrimidinecarboxylic, pyrazinecarboxamide, furikabutte, tailormake, isoxazolecarboxylic, thiazolidinedione, oxazolidinedione, imidazolidinecarboxamide, pyrrolidinylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl, piperazinylcarbonyl, tetrahydropyranyloxy, tetrahydropyranyl is ylamino, isopropylamino, diisopropylamino, dibutylamino; aralkylamines groups, such as benzylamino, dibenzylamino; heterocyclization amino groups, such as imidazolidinone, N-methyl-N-imidazolinone, thiazolidine, N-methyl-N-thiazolidinone, isothiazolinone, pyrazolinone, triethylamine, N-methyl-N-triethylamine, pyrrolidine, pyridylamino, N-methyl-N-pyridylamino, piperidylamine, pyrimidinamine, pyrazinamide, pyrilamine, thienylene, isoxazolidine, diazolidinylurea, oxazolidinedione, imidazolidinedione, pyrrolidinium, N-methyl-N-pyrrolidinium, piperidylamine, morpholinium, N-methyl-N-morpholinium, tetrahydrofurfurylamine, tetrahydropyrimidine; optionally substituted with halogen, alkylsulfonyl groups, such as methanesulfonamide, N-methyl-N-methanesulfonamido, ethanolamine, n-propanesulfonate, triftormetilfullerenov; arylsulfonyl groups, such as phenylcarbonylamino, N-methyl-N-phenylcarbonylamino, N-(4-chlorophenylsulfonyl)-N-methylamino, naphthalenemethylamine; acylamino groups, such as formylamino, acetylamino, N-methyl-N-acetylamino, propionamido, bucillamine, isobutylamino, N-methyl-N-isobutylamino, trimethylethylenediamine group, such as phenylacetylamino, N-methyl-N-phenylacetylamino, 2-phenylpropionylamino, 3 phenylbutyramide, diphenylacetylene, naphthylenediamine; amino group substituted by the groups they represent-CO-Het where Het represents a heterocycle), such as imidazolecarboxamide; N-methyl-N-imidazolecarboxamide, thiazolecarboxamide, N-methyl-N-thiazolecarboxamide, pyridylcarbonyl, N-methyl-N-pyridylcarbonyl, pyrimidinecarbonitrile, N-methyl-N-pyrimidinecarbonitrile, pyrazinecarboxamide, N-methyl-N-pyrazinecarboxamide, shrinkability, taylorsville, N-methyl-N-taylorsville, N-methyl-N-oxazolidinone, N-methyl-N-tetrachloroaniline, thiazolidinediones, oxazolidinecarboxylate, imidazolidinylideneamino, pyrrolidinylcarbonyl, piperidinylcarbonyl; alkoxycarbonyl groups, such as methoxycarbonylamino, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, tert-butoxycarbonylamino and N-methyl-N-(tert-butoxycarbonyl)amino; aryloxypropanolamine groups, such as phenoxycarbonylamino, naphthalenemethylamine; arachidonoylethanolamine groups, such as benzyloxycarbonylamino, famine; formyl; carboxyl; alkoxycarbonyl groups, such as methoxycarbonyl, etoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl and tert-butoxycarbonyl; aryloxyalkyl groups, such as phenoxycarbonyl and naphthalocyanines; aracelikarsaalyna groups, such as benzyloxycarbonyl, ventilatsioonil, phenylpropanolamine, benzylaminocarbonyl and naphthylenediamine; acyl groups such as acetyl, propionyl, butyryl and isobutyryl; arylcarbamoyl groups such as benzoyl and afterburner; groups that represent-CO-Het where Het represents a heterocycle) such as imidazolidinyl, thiazolidinones, isothiazolinones, pyrazolidinone, triazolylmethyl, pyrrolidinones, pyridylcarbonyl, pyrimidinylidene, PersonalCabinet, fullcarbon, thienylboronic, isoxazolidinone, thiazolidinediones, oxazolidinediones, imidazolidinedione, pyrrolidinylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl, piperazinylcarbonyl and 1,3,4-trihydroxypurine-2-ylcarbonyl; carbamoyl groups, such as carbarnoyl, methylcarbamoyl, dimethylcarbamoyl, ethylcarbitol, diethylcarbamoyl, propellerblades, dipropylamino, cyclopropanecarbonyl, benzylcarbamoyl, N-benzyl-N-methylcarbamoyl, N-methyl-N-phenetically, dibenzylamino, imidazolylalkyl, N-imidazolyl-N-methylcarbamoyl, N-benzimidazolyl-N-methylcarbamoyl, thiazolecarboxamide, N-methyl-N-thiazolecarboxamide, benzothiazolylthio, N-benzothiazolyl-N-methylcarbamoyl, isothiazolinones, oxazolidinyl, N-methyl-N-oxazolidinyl, benzoxazolinone, N-benzoxazolyl-N-methylcarbamoyl, personalberater, triazolylmethyl, pyrrolidino, pyridylcarbinol, N-methyl-N-pyridylcarbinol, N-methyl-N-(pyridylmethyl)carbarnoyl, pyrimidinecarbonitrile, pyrazinecarboxamide, fullcarbon, taylornol, isoxazolecarboxylic, diazolidinylurea, oxazolidinediones, imidazolidinecarboxamide, pyrrolidinylcarbonyl, piperidinylcarbonyl, tetrahydrofuranyl and tetrahydropyranyloxy; groups that represent A=CH(CH2)n- (where a represents the alicyclic heterocycle, "= " represents a double bond and n is 0, 1 or 2), such as (3,5-dioxo-2,4-thiazolidinedione)methyl, (3,5-dioxo-2,4-oxazolidinedione)methyl, (2,5-dioxoimidazolidin-4-ilidene)methyl, (5-oxo-3-thioxo-2,4-thiazolidinedione)methyl, (2,4,6-trioxo-3,5-desapariciones is B>2)mO- (where a represents the alicyclic heterocycle, "=" represents a double bond and m is 1, 2, or 3), such as 2-(3,5-dioxo-2,4-thiazolidinedione) ethoxy, 2-(3,5-dioxo-2,4-oxazolidinedione)ethoxy, 2-(2,5-dioxoimidazolidin-4-ilidene)ethoxy, 2-(5-oxo-3-thioxo-2,4-thiazolidinedione)ethoxy, 2-(2,4,6-trioxo-3,5-disabilityrelated)ethoxy and 2-(3,5-dimethyl-2,4,6-trioxo-3,5-disabilityrelated)ethoxy; and the groups that represent AND-SO2(CH2)m- (where a represents a heterocycle alicyclic and m has a value of 1, 2, or 3), such as (3,5-dioxo-2,4-thiazolidine) sulfanilyl, (3,5-dioxo-2, 4-oxazolidinyl)sulfanilyl, (2,5-dioxoimidazolidin-4-yl)sulfonylated, and (5-oxo-3-thioxo-2,4-thiazolidine)sulfanilyl.

As preferred groups for R4amay be especially mentioned, for example, hydrogen, nitro, cyano, bromine, imidazolyl, thiazolyl, pyridyl, pyrimidinyl, furyl, thienyl, morpholinyl, piperazinil, hydroxyl, pyrrolidinyloxy, piperidinyloxy, methansulfonate, tripterocalyx, vinylsulfonate, atomic charges, benzoyloxy, imidazolidinone, thiazolidinone, pyridylcarbonyl, pyrimidinecarboxylic, pyrazinecarboxamide, dimatia, N-methyl-N-methanesulfonamido, phenylcarbonylamino, N-methyl-N-phenylcarbonylamino, N-methyl-N-acetylamino, N-methyl-N-isobutylamino, N-methyl-N-benzoylamine, N-methyl-N-phenylacetylamino, N-methyl-N-taylorsville, N-methyl-N-thiazolecarboxamide, N-methyl-N-taylorsville, N-methyl-N-oxazolidinone, N-methyl-N-tetrachloroaniline, N-methyl-N-pyridylcarbonyl, N-methyl-N-pyrazinecarboxamide, N-methyl-N-pyrimidinecarbonitrile, N-methyl-N-(tert-butoxycarbonyl)amino, dimethylcarbamoyl, cyclohexylcarbonyl, phenylcarbamoyl, N-methyl-N-phenylcarbamoyl, N-benzyl-N-methylcarbamoyl, imidazolylalkyl, benzimidazolecarbamic, thiazolecarboxamide, N-methyl-N-thiazolecarboxamide, benzothiazolylthio, isothiazolinones, personalberater, triazolylmethyl, pyrrolidino, pyridylcarbinol, N-methyl-N-pyridylcarbinol, pyrimidinecarbonitrile, pyrazinecarboxamide, isoxazolecarboxylic, piperidinylcarbonyl, 1,3,4-trihydroxyphenyl-2-ylcarbonyl, formyl, carboxyl, methoxycarbonyl, etoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, tert-butoxycarbonyl, acetyl, benzoyl, (3,5-dioxo-2,4-thiazolidinedione)methyl, (3,5-dioxo-2,4-oxazolidinedione)methyl, (2,5-dioxoimidazolidin-4-ilidene)methyl) - Rev. den)ethoxy, 2-(2,5-dioxoimidazolidin-4-ilidene)ethoxy, 2-(5-oxo-3-thioxo-2,4-thiazolidinedione)ethoxy, (3,5-dioxo-2,4-thiazolidinedione)sulfanilyl, (3,5-dioxo-2,4-oxazolidinyl)sulfanilyl, (2,5-dioxoimidazolidin-4-yl)sulfonylated and (5-oxo-3-thioxo-2,4-thiazolidine)sulfanilyl. As a particularly preferred groups for R4acan be particularly noted, for example, hydrogen, nitro, cyano, bromine, thienyl, piperazinil, tripterocalyx, vinylsulfonate, atomic charges, dimethylamino, dibenzylamino, N-methyl-N-methanesulfonamide, N-methyl-N-phenylcarbonylamino, N-methyl-N-acetylamino, N-methyl-N-isobutylamino, N-methyl-N-benzoylamine, N-methyl-N-phenylacetylamino, N-methyl-N-taylorsville, N-methyl-N-oxazolidinedione, N-methyl-N-thiazolecarboxamide, N-methyl-N-pyridylcarbonyl, thiazolecarboxamide, benzothiazolylthio, benzimidazolecarbamic, N-methyl-N-phenylcarbamoyl, 1,3,4-trihydroxyphenyl-2-ylcarbonyl, methoxycarbonyl, isopropoxycarbonyl, and (3,5-dioxo-2,4-thiazolidinedione)methyl.

When R4is an R4bmay be cited as typical examples of the substituents are alkoxy groups containing from 1 to 4 carbon atoms, as R4bfor example, ATO such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl; aryl groups containing from 6 to 10 carbon atoms, such as phenyl, AMINOPHENYL and naphthyl; heterocyclic compounds such as imidazolyl, N-tosylimines, thiazolyl, 2-(morpholinomethyl)thiazolyl, isothiazolin, pyrazolyl, triazolyl, tetrazolyl, pyrrolyl, pyridyl, 2-methoxyphenyl, 5-hydroxypyridine, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, thienyl, 2-(morpholinomethyl)thienyl, oxazolyl, 2-phenyloxazolyl, isoxazolyl, diazolidinyl, oxazolidinyl, imidazolidinyl, pyrrolidinyl, piperidyl, morpholinyl, piperazinil, tetrahydrofuryl, tetrahydropyranyl and DIOXOLANYL; HE; alkoxy groups containing from 1 to 4 carbon atoms such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy, isopentane, 3-pentyloxy, 2, 2 DIMETHYLPROPANE, p-hexyloxy, 4-methylpentane and 2 ethylbutane; aryloxy group containing from 6 to 10 carbon atoms, such as phenoxy, naphthyloxy; benzyloxy; groups they represent-O-Het where Het represents a heterocycle) such as pyridyloxy, piperidinyloxy; acyloxy group containing from 1 to 5 carbon atoms, such as formyloxy, atomic charges, propionyloxy, BCIE as benzoyloxy, naftiliaki; phenylacetylene; groups that represent-O-CO-Het where Het represents a heterocycle) such as imidazolidinone, thiazolidinone, isothiazolinones, pyrazolylborate, triazolinones, pyrrolidinone, pyridylcarbonyl, pyrimidinecarboxylic, pyrazinecarboxamide, furikabutte, tailormake, isoxazolecarboxylic, thiazolidinedione, oxazolidinedione, imidazolidinecarboxamide, pyrrolidinylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl, piperazinylcarbonyl, tetrahydropyranyloxy, tetrahydropyranyloxy;

amino; monosubstituted or disubstituted amino groups such as methylamino, dimethylamino, ethylamino, diethylamino, propylamino, dipropylamino, isopropylamino, diisopropylamino, dibutylamino, benzylamino, dibenzylamino, 2-hydroxy-2-phenethylamine, 2-hydroxy-3-phenoxypropylamine, imidazolinone, thiazolidine, isothiazolinone, pyrazolinone, triethylamine, pyrrolidine, pyridylamino, piperidylamine, pyrimidinamine, pyrazinamide, pyrilamine, thienylene, isoxazolidine, diazolidinylurea, oxazolidinedione, imidazolidinedione, pyrrolidinium, piperidylamine, tetrahydrofurfurylamine, tetrahydropyrimidine; neobyazatelnostyu, ethanolamine, n-propanesulfonate, triftormetilfullerenov; phenylcarbonylamino; acylamino group containing from 1 to 5 carbon atoms, such as dimethylaminopropylamine, methylmonoethanolamine, formylamino, acetylamino, propionamido, bucillamine, isobutylamino, trimethylenediamine; arylcarboxylic group containing from 7 to 11 carbon atoms, such as benzoylamine, nattermannallee; phenylacetylamino; groups that represent-NH-CO-Het where Het represents a heterocycle) such as imidazolecarboxamide, thiazolecarboxamide, isoxazolecarboxylic, pyridylcarbonyl, pyrimidinecarbonitrile, pyrazinecarboxamide, shrinkability, taylorsville, pyrrolidinylcarbonyl, piperidinecarboxylate, morpholinylcarbonyl; alkoxycarbonyl group containing from 2 to 5 carbon atoms, such as methoxycarbonylamino, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl and tert-butoxycarbonylamino; benzyloxycarbonylamino; formyl; carboxy; alkoxycarbonyl group containing from 2 to 5 carbon atoms, such as methoxycarbonyl, etoxycarbonyl, n-propoxycarbonyl, isopropoxide is in carbon, such as acetyl, propionyl, butyryl and isobutyryl; groups that represent-CO-Het where Het represents a heterocycle) such as imidazolidinyl, thiazolidinones, isothiazolinones, pyrazolidinone, triazolylmethyl, pyrrolidinones, pyridylcarbonyl, pyrimidinylidene, PersonalCabinet, fullcarbon, thienylboronic, isoxazolidinone, thiazolidinediones, oxazolidinediones, imidazolidinedione, pyrrolidinylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl and piperazinylcarbonyl; groups that represent-CO-O-Het where Het represents a heterocycle) such as pyridylcarbonyl and piperidinylcarbonyl; and carbamoyl groups, such as carbarnoyl, methylcarbamoyl, dimethylcarbamoyl, ethylcarbitol, diethylcarbamoyl, propellerblades, dipropylamino, benzylcarbamoyl, dibenzylamino, imidazolylalkyl, thiazolecarboxamide, isothiazolinones, personalberater, triazolylmethyl, pyrrolidino, pyridylcarbinol, pyrimidinecarbonitrile, pyrazinecarboxamide, fullcarbon, taylornol, isoxazolecarboxylic, diazolidinylurea, oxazolidinediones, imidazolidinecarboxamide, pyrrolidinylcarbonyl, piperine groups for R4bmay be especially mentioned, for example, saturated or unsaturated alkoxy group such as methoxy, 2-propenyloxy, 2-butenyloxy, 3 hexenoate, 5-hexenoate and 2,2-DIMETHYLPROPANE; substituted with halogen, alkoxy groups such as 2-bromoethoxy and 2 chloroethoxy; cycloalkyl-alkoxy groups, such as cyclopentyloxy, cyclohexylmethoxy; aryl-alkoxy group, such as benzyloxy, aminobenzoate, Chlorobenzilate, fermentelos, brombenzene, nitrobenzyloxy, (trifluoromethyl)benzyloxy, DICHLOROSILANE, dimethylbenzylamine, methoxybenzyloxy, sulfamoylbenzoic (methylendioxy)benzyloxy, carboxymethoxy, (ethoxycarbonyl)benzyloxy, n-butoxybenzoate, 3 phenylpropoxy, di(methoxyphenyl)methoxy, 2,2-diphenylethane, 1-methyl-1-phenylethane, aftermatket; heterocycle-substituted alkoxy groups such as titillate, 2-(morpholinomethyl)titillate, pyridyloxy, (5-hydroxypyridine)methoxy, (2-methoxyphenyl)methoxy, 2-(pyridyl)ethoxy, personalitati, pyrimidinylidene, N-totalmedia.exe, oxazolines, 2-phenyloxazolidine, thiazolidinone, 2-(morpholinomethyl)thiazoleacetate, (3,5-dioxo-2,4-thiazolidine)methoxy, N-methylpiperidine, N-tert-buto is ethoxy, (3,3-dimethyl-2,4-DIOXOLANYL)methoxy, (1-methyl-3-oxetanyl)methoxy and 2-(morpholine-4-yl)ethoxy; alkoxy-alkoxy group, such as methoxymethyl and 2 ethoxyethoxy; benzyloxy, alkoxy groups such as 2-(benzyloxy)ethoxy; aryloxy-alkoxy groups such as 2-(atomic charges)ethoxy; alkylamino-alkoxy group such that represent bis(dimethylaminomethyl)methoxy; alkoxycarbonyl-alkoxy group, such as 4-(tert-butoxycarbonylamino)butoxy; and alkoxycarbonyl-alkoxy groups, such as ethoxycarbonylmethoxy, 2-(methoxycarbonyl)ethoxy and 5-(etoxycarbonyl)pentyloxy.

As a particularly preferred groups for R4bmay be especially mentioned, for example, methoxy, 2-propenyloxy, benzyloxy, aminobenzoate, Chlorobenzilate, fermentelos, (trifluoromethyl)benzyloxy, DICHLOROSILANE, dimethylbenzylamine, methoxybenzyloxy, sulfamoylbenzoic (methylendioxy)benzyloxy, carboxymethoxy, (ethoxycarbonyl)benzyloxy, n-butoxybenzoate, titillate, 2-(morpholinomethyl)titillate, pyridyloxy, (2-methoxyphenyl)methoxy, (5-hydroxypyridine)methoxy, 2-(pyridyl)ethoxy, personalitati, pyrimidinylidene, N-totalmedia.exe, oxazolines, 2-Fe is XI, N-methylpiperidine and methoxymethyl.

When R4is an R4cmay be cited as typical examples of the substituents are alkoxy groups containing from 1 to 4 carbon atoms, as R4cfor example, halogen atoms such as fluorine, chlorine, bromine, iodine; cycloalkyl group containing from 3 to 7 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl; aryl groups containing from 6 to 10 carbon atoms, such as phenyl and naphthyl; heterocyclic compounds, such as imidazolyl, thiazolyl, isothiazolin, pyrazolyl, triazolyl, tetrazolyl, pyrrolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, thienyl, oxazolyl, isoxazolyl, diazolidinyl, oxazolidinyl, 3,5-dioxoimidazolidin, imidazolidinyl, 2-Oxymetazoline, pyrrolidinyl, piperidyl, morpholinyl, pyrazolidine, 3,5-dioxopiperazinyl, piperazinil, 2.5-dioxopiperazinyl, tetrahydrofuryl, tetrahydropyranyl and DIOXOLANYL; -SH; -HE; alkoxy groups containing from 1 to 4 carbon atoms, such as methoxy, ethoxy, n-propoxy, isopropoxy, p-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy, isopentane, 3-pentyloxy, 2,2-DIMETHYLPROPANE, n-hexyloxy, 4-methylpentanoate; groups that represent-O-Het where Het represents a heterocycle) such as pyridyloxy, piperidinyloxy; acyloxy group containing from 1 to 5 carbon atoms, such as formyloxy, atomic charges, propionyloxy, butyryloxy, isobutyryloxy, trimethylsilyloxy; arylcarboxylic group containing from 7 to 11 carbon atoms, such as benzoyloxy, naftiliaki; vinylacetylene; groups that represent-O-CO-Het where Het represents a heterocycle) such as imidazolidinone, thiazolidinone, isothiazolinones, pyrazolylborate, triazolinones, pyrrolidinone, pyridylcarbonyl, pyrimidinecarboxylic, pyrazinecarboxamide, furikabutte, tailormake, isoxazolecarboxylic, thiazolidinedione, oxazolidinedione, imidazolidinecarboxamide, pyrrolidinylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl, piperazinylcarbonyl, tetrahydropyranyloxy, tetrahydropyranyloxy; amino; monosubstituted or disubstituted amino groups such as methylamino, dimethylamino, ethylamino, 2-hydroxy-2-phenethylamine, 2-hydroxy-3-phenoxypropylamine, di ethylamino, propylamino, dipropylamino, isopropylamino, diisopropylamino, dibutylamino, benzylamino, dibenzylamino, piperidylamine, pyrimidinamine, pyrazinamide, pyrilamine, thienylene, isoxazolidine, diazolidinylurea, oxazolidinedione, imidazolidinedione, pyrrolidinium, piperidylamine, tetrahydrofurfurylamine, tetrahydropyrimidine; optionally substituted with halogen, alkylsulfonyl group containing from 1 to 4 carbon atoms, such as methanesulfonamido, ethanolamine, n-propanesulfonate, triftormetilfullerenov; phenylcarbonylamino; acylamino group containing from 1 to 5 carbon atoms, such as formylamino, acetylamino, propionamido, bucillamine, isobutylamino, trimethylenediamine; arylcarboxylic group containing from 7 to 11 carbon atoms, such as benzoylamine, 4-chlorobenzylamino, nattermannallee; phenylacetylamino; groups that represent-NH-CO-Het where Het represents a heterocycle) such as imidazolecarboxamide, thiazolecarboxamide, pyridylcarbonyl, pyrimidinecarbonitrile, pyrazinecarboxamide, shrinkability, taylorsville, thiazolidinediones, oxazolidinecarboxylate, imidazolidinylideneamino, pyrrolidinylcarbonyl, piperidinylcarbonyl; alkoxycarbonylmethyl, isopropoxycarbonyl and tert-butoxycarbonylamino; benzyloxycarbonylamino; formyl; carboxyl; alkoxycarbonyl group containing from 2 to 5 carbon atoms, such as methoxycarbonyl, etoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl and tert-butoxycarbonyl; phenoxycarbonyl; benzyloxy carbonyl; acyl group containing from 2 to 5 carbon atoms, such as acetyl, propionyl, butyryl and isobutyryl; groups that represent-CO-Het where Het represents a heterocycle) such as imidazolidinyl, thiazolidinones, isothiazolinones, pyrazolidinone, triazolylmethyl, pyrrolidinones, pyridylcarbonyl, pyrimidinylidene, PersonalCabinet, fullcarbon, thienylboronic, isoxazolidinone, thiazolidinediones, oxazolidinediones, imidazolidinedione, pyrrolidinylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl and piperazinylcarbonyl; groups that represent-CO-O-Het where Het represents a heterocycle) such as pyridylcarbonyl and piperidinylcarbonyl; and carbamoyl groups, such as carbarnoyl, methylcarbamoyl, dimethylcarbamoyl, ethylcarbitol, diethylcarbamoyl, propellerblades, dipropylamino, benzylcarbamoyl, dellicarpini, pyrrolidino, pyridylcarbinol, pyrimidinecarbonitrile, pyrazinecarboxamide, fullcarbon, taylornol, isoxazolecarboxylic, diazolidinylurea, oxazolidinediones, imidazolidinecarboxamide, pyrrolidinylcarbonyl, piperidinylcarbonyl, tetrahydrofuranyl and tetrahydropyranyloxy.

As preferred groups for R4cmay be especially mentioned, for example, phenethyl, -hydroxybenzyl, 1-(atomic charges)and ethyl (3,5-dioxo-2,4-thiazolidine)methyl.

So, as a typical preferred combinations for R1, R2, R3and R4can be given those in which, for example, R1represents methyl, ethyl, or isopropyl, R2represents acetyl or propionyl group having a Deputy selected from the group comprising phenyl, phenoxy, amino, tert-butoxycarbonylamino, benzyloxycarbonylamino, (benzyloxycarbonyl)-N-methylamino, acetylamino and morpholinylcarbonyl; or hydrogen, acetyl, propionyl, isobutyryl, benzoyl, pyridylcarbonyl, pyrrolidinylcarbonyl, fullcarbon, methanesulfonyl, or trifloromethyl, R3represents methyl, ethyl, isopropyl, n-pentyl, cyclopentyl is Livonians, vinylsulfonate, atomic charges, dimethylamino, dibenzylamino, N-methyl-N-methanesulfonamide, N-methyl-N-phenylcarbonylamino, N-methyl-N-acetylamino, N-methyl-N-isobutylamino, N-methyl-N-benzoylamine, N-methyl-N-phenylacetylamino, N-methyl-N-imidazolecarboxamide, N-methyl-N-thiazolecarboxamide, N-methyl-N-pyridylcarbonyl, N-methyl-N-pyrimidinecarbonitrile, N-methyl-N-pyrazinecarboxamide, N-methyl-N-taylorsville, N-methyl-N-oxazolidinone, N-methyl-N-(tert-butoxycarbonyl)amino, thiazolecarboxamide, methoxycarbonyl, isopropoxycarbonyl, (3,5-dioxo-2,4-thiazolidinedione)methyl, methoxy, 2-propenyloxy, benzyloxy, aminobenzoate, Chlorobenzilate, fermentelos, (trifluoromethyl)benzyloxy, DICHLOROSILANE, dimethylbenzylamine, methoxybenzyloxy, sulfamoylbenzoic (methylendioxy)benzyloxy, carboxymethoxy, (ethoxycarbonyl)benzyloxy, n-butoxybenzoate, titillate, 2-(morpholinomethyl)titillate, pyridyloxy, (2-methoxyphenyl)methoxy, 2-(pyridyl)ethoxy, personalitati, pyrimidinylidene, N-totalmedia.exe, oxazolines, 2-phenyloxazolidine, thiazolidinone, 2-(morpholinomethyl)thiazoleacetate, (3,5-dioxo-2,4-thiazolidine)methoxy, N-methylpiperidin>/P>As typical examples of the compounds represented by structural formula (1) above may be given the compounds that are included in the experimental part of the description, can also be included the following connections:

6-(benzofuran-2-yl)-3-ethyl-4-hydroxy-5-methyl-2H-Piran-2-he;

6-(benzofuran-2-yl)-4-hydroxy-5-methyl-3-n-propyl-2H-Piran-2-he;

4 atomic charges-6-(benzofuran-2-yl)-5-ethyl-3-methyl-2H-Piran-2-he;

4 atomic charges-6-(benzofuran-2-yl)-5-isopropyl-3-methyl-2H-Piran-2-he;

6-(benzofuran-2-yl)-4-(2-(tert-butoxycarbonylamino)atomic charges)-5-ethyl-3-methyl-2H-Piran-2-he;

6-(benzofuran-2-yl)-5-ethyl-3-methyl-4-(2-pyrrolidone-5-icebox)-2H-Piran-2-he;

4-(2-aminoethoxy)-6-(benzofuran-2-yl)-5-ethyl-3-methyl-2H-Piran-2-he;

4-(3-acetylamino-4-morpholinyl-4-oxobutyrate)-6-(benzofuran-2-yl)-5-ethyl-3-methyl-2H-Piran-2-he;

6-(benzofuran-2-yl)-3,5-dimethyl-4-propionyloxy-2H-Piran-2-he;

6-(benzofuran-2-yl)-5-ethyl-4-isobutyryloxy-3-methyl-2H-Piran-2-he;

6-(benzofuran-2-yl)-3,5-dimethyl-4-isovalerianic-2H-Piran-2-he;

6-(benzofuran-2-yl)-3,5-dimethyl-4-(2,2,2-trimethylsilyloxy)-2H-Piran-2-he;

6-(benzofuran-2-yl)-4-cyclohexylmethoxy-3,5-dimethyl-2H-Piran-2-he;

6-(benzofuran-2-yl)-4-(2-cyclopropyl
6-(benzofuran-2-yl)-4-benzoyloxy-5-ethyl-3-methyl-2H-Piran-2-he;

6-(benzofuran-2-yl)-4-benzoyloxy-5-isopropyl-3-methyl-2H-Piran-2-he;

6-(benzofuran-2-yl)-3,5-dimethyl-4-naftiliaki-2H-Piran-2-he;

6-(benzofuran-2-yl)-3,5-dimethyl-4-imidazolidinone-2H-Piran-2-he;

6-(benzofuran-2-yl)-3,5-dimethyl-4-thiazolidinone-2H-Piran-2-he;

6-(benzofuran-2-yl)-3,5-dimethyl-4-thiazolidinone-2H-Piran-2-he;

6-(benzofuran-2-yl)-5-ethyl-3-methyl-4-pyridylcarbonyl-2H-Piran-2-HE;

6-(benzofuran-2-yl)-3,5-dimethyl-4-pyrimidinecarboxylic-2H-Piran-2-he;

6-(benzofuran-2-yl)-3,5-dimethyl-4-pyrazinecarboxamide-2H-Piran-2-he;

6-(benzofuran-2-yl)-3,5-dimethyl-4-thienylboronic-2H-Piran-2-he;

6-(benzofuran-2-yl)-3,5-dimethyl-4-isoxazolecarboxylic-2H-Piran-2-he;

6-(benzofuran-2-yl)-3,5-dimethyl-4-(2-imidazolidinethione)-2H-Piran-2-he;

6-(benzofuran-2-yl)-3,5-dimethyl-4-(2-pyridylacetate)-2H-Piran-2-he;

6-(benzofuran-2-yl)-3,5-dimethyl-4-(2-methoxyethoxy)-2H-Piran-2-he;

6-(benzofuran-2-yl)-3,5-dimethyl-4-(2-tert-butoxyethoxy)-2H-Piran-2-he;

6-(benzofuran-2-yl)-4-hydroxy-3-methyl-5-n-propyl-2H-Piran-2-he;

6-(benzofuran-2-yl)-5-cyclopentyl-4-hydroxy-3-methyl-2H-Piran-2-he;

6-(benzofuran-2-yl)-5-cyclopropylmethyl-4-hydroxy-3-methyl-2H-p the Roxy-3-methyl-5-naphthylmethyl-2H-Piran-2-he;

6-(benzofuran-2-yl)-5-ethoxy-4-hydroxy-3-methyl-2H-Piran-2-he;

6-(benzofuran-2-yl)-4-hydroxy-5-isopropoxy-3-methyl-2H-Piran-2-he;

4 atomic charges-3,5-dimethyl-6-(5-(2-thienyl)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-6-(5-((3,5-dioxo-2,4-oxazolidinedione)methyl)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-6-(5-((2,5-dioxoimidazolidin-4-ilidene)methyl)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-((5-oxo-3-thioxo-2,4-thiazolidinedione)methyl)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-((2,4,6-trioxo-3,5-disabilityrelated)methyl)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-6-(5-((3,5-dimethyl-2,4,6-trioxo-6,5-disabilityrelated)methyl)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-6-(5-(2-(3,5-dioxo-2,4-thiazolidinedione)ethoxy)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-6-(5-(2-(3,5-dioxo-2,4-oxazolidinedione)ethoxy)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-6-(5-(2-(2,5-dioxoimidazolidin-4-ilidene)ethoxy)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(2-(5-oxo-3-thioxo-2,4-thiazolidinedione)ethoxy)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(2-(2,4,6-trioxo-3,5-disabilityrelated)ethoxy)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-6-(5-((3,5-dioxo-2,4-thiazolidine)sulfanilyl)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-6-(5-((3,5-dioxo-2,4-oxazolidinyl)sulfanilyl)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-6-(5-((2,5-dioxoimidazolidin-4-yl)sulfanilyl)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-((5-oxo-3-thioxo-2,4-thiazolidine)sulfanilyl)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-6-(5-((3,5-dioxo-2,4-thiazolidine)methoxy)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-6-(5-((3,5-dioxo-2,4-oxazolidinyl)methoxy)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-6-(5(2,5-dioxoimidazolidin-4-yl)methoxy)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-((5-oxo-3-thioxo-2,4-thiazolidine)methoxy)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-((2,4,6-trioxo-3,5-desapariciones)methoxy)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-6-(5-((3,5-dimethyl-2,4,6-trioxo-3,5-desapariciones)methoxy)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(N-methyl-N-phenylcarbamoyl)benzofuran-2-yl)-2H-Piran-2-he;

6-(5-(N-benzyl-N-methylcarbamoyl)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(N-methyl-N-pyridi who yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(N-methyl-N-(pyridylmethyl)carbarnoyl)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(2-(2-hydroxy-2-phenethylamine)ethoxy)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(2-(2-hydroxy-3-phenoxypropylamine)ethoxy)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(2-hydroxy-3-aminopropoxy)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(2-hydroxy-3-phenylaminopropyl)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(3-(2-hydroxy-2-phenethylamine)propyl)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(3-(2-hydroxy-3-phenoxypropylamine)propyl)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(2-(2-hydroxy-2-phenethylamine)ethyl)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(2-(2-hydroxy-3-phenoxypropylamine)ethyl)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-6-(5-(3,5-dioxopiperidin-4-ylmethyl)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-6-(5-(3,5-dioxoimidazolidin-4-ylmethyl)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(2-Oxymetazoline)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-6-(5-(2,5-dioxopiperazinyl)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-4-Ki-is-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(6-oxo-4,5-benzoxazin-2-yl)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(3-pyridylmethyl)benzofuran-2-yl)-2H-Piran-2-he;

6-(5-(4-bromo-2-cyanovinylene)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(N-methyl-N-(3-pyridyl)aminomethyl)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(N-methyl-N-(3-pyridyl)carbarnoyl)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(4-(2-pyridyl)piperazinylcarbonyl)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(4-(2-pyrimidinyl)piperazinylcarbonyl)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(N-methyl-N-(2-pyridyl)carbarnoyl)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(N-(2-pyrimidinyl)carbarnoyl)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-((2-pyridylmethyl)carbarnoyl)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(triazolylmethyl)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-6-(5-(2,5-dioxopiperazinyl)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-6-(5-(2,6-dioxopiperidin)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-6-(5-(2,3-dioxopiperazinyl)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he;

6-(5-(2-(4-chlorobenz the l)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(3-(2-pyrazinecarboxamide)propoxy)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(3-(2-pyridylcarbonyl)propoxy)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(3-(5-isoxazolecarboxylic)propoxy)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(3-(morpholinylcarbonyl)propoxy)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(3-(methanesulfonamido)propoxy)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-6-(5-(3-(dimethylaminomethylene)propoxy)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(3-(isoxazolecarboxylic)propoxy)benzofuran-2-yl)-2H-Piran-2-he;

6-(5-(N-acetylpiperidine-3-ylethoxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(N-(2-pyridylcarbonyl)piperidine-3-ylethoxy)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(N-(2-pyrazinecarboxamide)piperidine-3-ylethoxy)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(N-(5-isoxazolidinone)piperidine-3-ylethoxy)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(N-(morpholinylcarbonyl)piperidine-3-ylethoxy)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(N-methanol-3-ylethoxy)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(N-(5-triazolylmethyl)piperidine-3-ylethoxy)benzofuran-2-yl)-2H-Piran-2-he;

and 3,5-dimethyl-4-hydroxy-6-(5-(N-(5-isoxazolidinone)piperidine-3-ylethoxy)benzofuran-2-yl)-2H-Piran-2-it.

As a preferred characteristic of the compounds, which are compounds of structural formula (I), above, may be provided, for example, the following:

4 atomic charges-6-(benzofuran-2-yl)-3,5-dimethyl-2H-Piran-2-he;

6-(benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he;

6-(benzofuran-2-yl)-4-benzoyloxy-3,5-dimethyl-2H-Piran-2-he;

6-(benzofuran-2-yl)-3,5-dimethyl-4-methanesulfonate-2H-Piran-2-he;

6-(benzofuran-2-yl)-3,5-dimethyl-4-(2-pyridylcarbonyl)-2H-Piran-2-he;

3,5-dimethyl-6-(5-((3,5-dioxo-2,4-thiazolidinedione)methyl)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-6-(5-((3,5-dioxo-2,4-thiazolidine)methyl)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he;

6-(benzofuran-2-yl)-4-hydroxy-3-methyl-5-n-pentyl-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-methoxybenzophenone-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(7-methoxybenzophenone-2-yl)-2H-Piran-2-he;

4 atomic charges-3,5-dimethyl-6-(6-(tripterocalyx)benzofuran-2-yl)-2H-Piran-2-he;

4 atomic charges-3,5-dimethy
3,5-dimethyl-4-hydroxy-6-(5-(5-pyrimidinylidene)benzofuran-2-

yl)-2H-Piran-2-he;

6-(benzofuran-2-yl)-3,5-dimethyl-4-(4-hydroxymethylbutyrate)-2H-Piran-2-he;

6-(benzofuran-2-yl)-4-(2-(N-carbobenzoxy-N-methylamino)atomic charges)-3,5-dimethyl-2H-Piran-2-he;

6-(benzofuran-2-yl)-3,5-dimethyl-4-(4-methoxybenzyloxy)-2H-Piran-2-he;

6-(benzofuran-2-yl)-3,5-dimethyl-4-(2-phenylacetylene)-2H-Piran-2-he;

6-(benzofuran-2-yl)-5-ethyl-4-hydroxy-3-methyl-2H-Piran-2-he;

6-(benzofuran-2-yl)-4-hydroxy-5-isopropyl-3-methyl-2H-Piran-2-he;

6-(benzofuran-2-yl)-5-benzyl-4-hydroxy-3-methyl-2H-Piran-2-he;

6-(benzofuran-2-yl)-3,5-dimethyl-4-isobutyryloxy-2H-Piran-2-he;

4 atomic charges-3,5-dimethyl-6-(5-nitrobenzophenone-2-yl)-2H-Piran-2-he;

6-(benzofuran-2-yl)-3,5-dimethyl-4-(2-phenoxyethoxy)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-nitrobenzophenone-2-yl)-2H-Piran-2-he;

3,5-dimethyl-6-(5-(dimethylamino)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he;

6-(5-(dibenzylamino)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(N-methyl-N-(2-thienylboronic)amino)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(N-methyl-N-(3-pyridylcarbonyl)amino)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(N-isobutyl the h-2-yl)-2H-Piran-2-he;

6-(5-(N-benzoyl-N-methylamino)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he;

6-(5-(N-tert-butoxycarbonyl-N-methylamino)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he;

6-(5-(benzothiazolylthio)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he;

6-(5-(benzimidazolecarbamic)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(N-methyl-N-phenylcarbamoyl)benzofuran-2-yl)-2H-Piran-2-he;

6-(5-(N-(4-chlorophenylsulfonyl)-N-methylamino)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(1,3,4-trihydroxyphenyl-2-ylcarbonyl)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-morpholinomethyl-2-yl)-2H-Piran-2-he;

6-(benzofuran-2-yl)-3,5-dimethyl-4-isonicotinoyl-2H-Piran-2-he;

4-(2-aminoethoxy)-6-(benzofuran-2-yl)-3,5-dimethyl-2H-Piran-2-he;

6-(5-benzyloxybenzophenone-2-yl)-4-(2-(tert-butoxycarbonylamino)atomic charges)-3,5-dimethyl-2H-Piran-2-he;

4-(2-aminoethoxy)-6-(5-benzyloxybenzophenone-2-yl)-3,5-dimethyl-2H-Piran-2-he;

4-(4-(acetylamino)benzoyloxy)-6-(5-benzyloxybenzophenone-2-yl)-3,5-dimethyl-2H-Piran-2-he;

6-(5-benzyloxybenzophenone-2-yl)-3,5-dimethyl-4-nicotinergic-2H-Piran-2-he;

6-(5-benzyloxybenzophenone-2-yl)-3,5-dimethyl- 5-ethyl-4-hydroxy-3-methyl-6-(5-(3-pyridyloxy)benzofuran-2-yl)-2H-Piran-2-he;

4 atomic charges-3,5-dimethyl-6-(5-(2-thiazoleacetate)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(5-triazolylmethyl)benzofuran-2-yl)-2H-Piran-2-he;

4 atomic charges-6-(5-(2,4-dichloro-5-triazolylmethyl)benzofuran-2-yl)-3,5-dimethyl-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(2-(4-methyl-5-thiazolyl)ethoxy)benzofuran-2-yl)-2H-Piran-2-he;

4 atomic charges-3,5-dimethyl-6-(5-(2-(4-methyl-5-thiazolyl)ethoxy)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(4-methyl-5-thiazoleacetic)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(2-(morpholinomethyl)-5-triazolylmethyl)benzofuran-2-yl)-2H-Piran-2-he;

4 atomic charges-3,5-dimethyl-6-(5-(4-methyl-1-tosyl-5-imidazolylidene)benzofuran-2-yl)-2H-Piran-2-he;

6-(benzofuran-2-yl)-3,5-dimethyl-4-(3-phenylpropionylamino)-2H-Piran-2-he;

6-(benzofuran-2-yl)-3,5-dimethyl-4-(2-pyrolox)-2H-Piran-2-he;

6-(benzofuran-2-yl)-3,5-dimethyl-4-nicotinergic-2H-Piran-2-he;

6-(benzofuran-2-yl)-3,5-dimethyl-4-(2-acetylamino-4-(morpholine-4-yl)-4-oxobutyrate)-2H-Piran-2-he;

4 atomic charges-6-(5-bromobenzophenone-2-yl)-3,5-dimethyl-2H-Piran-2-he;

6-(benzofuran-2-yl)-5-cyclopentylmethyl-4-hydroxy-3-methyl-2H-Piran-2-he;

6-(benzofuran-2-yl)-4-(1-carbobenzoxy-2-pyrrolidone-5-icebox)-3,5-dimethyl-2H-feast of the t-butoxycarbonylamino)atomic charges)-3,5-dimethyl-2H-Piran-2-he;

6-(benzofuran-2-yl)-4-(2,4-dimethoxybenzoyl)-3,5-dimethyl-2H-Piran-2-he;

6-(benzofuran-2-yl)-3,5-dimethyl-4-(3-dimethylaminobenzoate)-2H-Piran-2-he;

4-(4-(acetylamino)benzoyloxy)-6-(benzofuran-2-yl)-3,5-dimethyl-2H-Piran-2-he;

3,5-dimethyl-6-(5-(2-forbindelse)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(3,4-(methylendioxy)benzyloxy)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(3-pyridyloxy)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(5-hydroxy-3-pyridyloxy)benzofuran-2-yl)-2H-Piran-2-he;

4 atomic charges-3,5-dimethyl-6-(5-(2-methoxy-5-pyridyloxy(benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(1-methylpiperidin-3-ylethoxy)benzofuran-2-yl)-2H-Piran-2-he;

6-(5-(4-carboxyphenoxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(2-(trifluoromethyl)benzyloxy)benzofuran-2-yl} -2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(3-(trifluoromethyl)benzyloxy)benzofuran-2-yl)-2H-Piran-2-he;

6-(5-(3,4-dimethylbenzylamine)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(2-teenrotica)benzofuran-2-yl)-2H-Piran-2-he;

4 atomic charges-3,5-dimethyl-6-(5-(2-teenrotica)benzofuran-2-yl)-2H-Piran-2-he;
4 atomic charges-3,5-dimethyl-6-(5-(2-(morpholinomethyl)-5-teenrotica)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(4-oxazolidinone)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(2-phenyl-4-oxazolidinone)benzofuran-2-yl)-2H-Piran-2-he;

6-(5-(2,4-dichloraniline)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he;

6-(5-(3,4-dichloraniline)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he;

6-(5-(4-n-butoxybenzoate)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(6-(1,2,3,4-tetrahydronaphthalen-1 yloxy)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(2-propyne-1-yloxy)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-6-(5-(3-forbindelse)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-6-(5-(4-forbindelse)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(3-methoxybenzyloxy)benzofuran-2-yl)-2H-Piran-2-he;

6-(5-(3-chlorobenzoyloxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he;

6-(5-(3-aminobenzoate)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he;

6-(5-(3-(tert-butoxycarbonylamino)benzyloxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he;

4 atomic charges-6-(5-(3- (tert-butoxycarbonylamino)benzyloxy-2-yl)-2H-Piran-2-he;

4 atomic charges-3,5-dimethyl-6-(5-(methoxycarbonyl)benzofuran-2-yl)-2H-Piran-2-he;

4 atomic charges-6-(4-benzyloxybenzophenone-2-yl)-3,5-dimethyl-2H-Piran-2-he;

4 atomic charges-6-(4-acetyloxybenzoic-2-yl)-3,5-dimethyl-2H-Piran-2-he;

4 atomic charges-3,5-dimethyl-6-(5-methoxybenzophenone-2-yl)-2H-Piran-2-he;

4 atomic charges-6-(5-benzyloxybenzophenone-2-yl)-3,5-dimethyl-2H-Piran-2-he;

6-(5-benzyloxybenzophenone-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he;

4 atomic charges-3,5-dimethyl-6-(5-p-toluensulfonate-2-yl)-2H-Piran-2-he;

4 atomic charges-6-(7-benzyloxybenzophenone-2-yl)-3,5-dimethyl-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(5-(methoxycarbonyl)benzofuran-2-yl)-2H-Piran-2-he;

3,5-dimethyl-4-hydroxy-6-(6-methoxyethoxymethyl-2-yl)-2H-Piran-2-it.

Compounds represented by structural formula (I), above, may in some cases to form an acid additive salt or basic additive salt. As typical examples of the acid additive salts can be in the acid additive salts of mineral acids such as hydrochloric acid, Hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, organic acids such as formic acid, acetic key is fumaric acid, maleic acid, lactic acid, malic acid, tartaric acid, citric acid, methanesulfonate and econsultation and acidic amino acids such as aspartic acid and glutamic acid; as typical examples of the basic additive salts can be mentioned salts of metals such as lithium, sodium or potassium; salts of divalent or trivalent metals, such as magnesium, calcium, zinc and aluminum; additive salts of basic amino acids such as lysine and arginine; as well as salts of ammonium or organic ammonium, such as methylammonium, dimethylammonium, ammonium, benzylamine and monoethanolamine.

The present invention also includes hydrates of the compounds represented by structural formula (I), as well as their different solvate and crystalline polymorphous forms.

Compounds according to the invention as a whole can be obtained using the processes disclosed below in part related to the production Processes from 1 to 5, with amendments, if necessary, modifications, and using the suitable starting compounds, reagents and conventional synthetic methods.

The process of obtaining 1 (see diagram 1 at the end of the description).

Nab the person shown in the diagram of the process of obtaining 1. A solution of 2,4-disubstituted-keeeper in THF, treated with 2 equivalents of a base, for example, 1 equivalent of NaH and 1 equivalent of n-BuLi, or 2 equivalents of LDA, for making dienoate, then the derived ether benzofuranol acid is injected with Venosta in condensation Claisen with intermediate digitalimage derived. Intermediate dictaphone derivative is subjected to alkaline hydrolysis and then treated with acid to obtain-pyrone. Intermediate dictaphone derivative can be subjected to alkaline hydrolysis with subsequent acid treatment, then the treatment with acetic anhydride and pyridine to obtain 4-atomic charges--Piron, which can then be re-subjected to alkaline hydrolysis, which leads to 4-hydroxy-pyrone. An alternative way to obtain 4-hydroxy-pyrone is to process the intermediate digitalimage derived by acid, such as sulfuric acid, polyphosphoric acid or p-Tson, or heated intermediate digitalimage derived under reduced pressure.

The process of obtaining 2 (see diagram 2 at the end of the description).

Intermediate dictaphone proizvodnja 2. Benzoperylene is treated with a base, such as LDA, getting enolate, which interacts with the ester of malonic acid such as the acid chloride of monomethylamine with intermediate digitalimage derived. An alternative way of intermediate dictaphone derivative can be obtained by carrying out the process in which the diketone obtained in the result of the interaction of the acid chloride or ester of the acid with benzopyrylium the enolate, treated with 2 equivalents of base, such as LDA, for making dienoate, which then reacts with CO2-related compound, such as carbon dioxide or dimethylcarbonate.

The process of obtaining 3 (see diagram 3 in the end of the description).

The derived benzofuran--Piron according to the present invention can also be obtained using the method presented in the diagram of the process of obtaining 3. The derived benzofuran-pyrone can be obtained by a method in which benzoperylene in the reaction, for example, with TMSCl-Et3or TMSOTf-Et3turns into the ether of silylene, and the latter interacts with dichlorohydrin malonic acid or fluids of malonic acid.

The process of the floor of the et can be obtained by way presents the diagram of the process of obtaining 4. The derived benzofuran-pyrone can be obtained by a method in which the derived-pyrone with the Deputy-CH2X at position C-6 (where X represents a leaving group such as Cl, Br, I, OMs or OTf) interacts with the substituted salicylic aldehyde in the presence of a base, such as2CO3and/or DBU.

The process of obtaining 5 (see diagram 5 in the end of the description).

Derivatives benzofuran--pyrone of the present invention, in which R2(where R2the group defined above) is a COR5or SO2R6(where R5and R6groups defined above), can be obtained using the method shown in the diagram of the process of obtaining 5. Of the derivatives of benzofuran--Piron related to the present invention, the derived benzofuran--Piron, in which the group R2represents-COR5can be obtained by a method in which the original connection, the derivative of 6-benzofuran-4-hydroxy-pyrone obtained using any of the above processes of obtaining 1-4, modified if necessary, interacts with the acid chloride or acid anhydride in prisutstvie, such as pyridine or imidazole, or an alternative way in which the original connection interacts with the carboxylic acid in the presence of a condensing agent such as WSC-HOBt, DCC-HOBt, CDI, diethylthiophosphate or diphenylphosphoryl, or a method of using the reaction Mitsunobu, where the original connection interacts with the carboxylic acid in the presence of RH3R-DD. Similarly derives benzofuran--Piron, where R2represents the SO2R6can be obtained by the interaction of the initial substance, 6-benzofuran-4-hydroxy-pyrone, with a derivative of sulphonylchloride representing RSO2Cl in the presence of a base, e.g. a tertiary amine such as Et3N, or nitrogen-containing aromatic heterocycle, such as pyridine or imidazole.

Derivatives benzofuran--Piron according to the invention, in which R4Deputy, as defined above other than a hydrogen atom, can be obtained using the method presented in the diagrams of the processes of obtaining 6 or 7. As shown in the diagram of the process of obtaining 6, in any of the processes of obtaining 1-5 above and modified, if necessary, to obtain entogo hydroxy-, methoxy-, formyl-, bromine-, nitro -, and so on, as the initial connection is readily available substituted derivative of salicylic aldehyde. The path And is a method, which includes the conversion of the functional group, hydroxy-, methoxy-, formyl-, bromine - or microsatellites on stage benzofuran--Piron, while the way In is the way in which the ring-pyrone design after the conversion of the functional group, R4at the stage of intermediate derived ether 2-benzofuranol acid.

The process of obtaining 6 (see diagram 6 in the end of the description).

The process of obtaining 7 (see diagram 7 in the end of the description).

The transformation of R4the functional groups of the hydroxy-, methoxy-, formyl-, bromine-, nitro -, etc. can be carried out using the method shown in the diagram of the process of getting a 7. For intermediate derived benzofuran--Piron, obtained along the way And in the process of getting 6, the transformation of the hydroxyl group in a functional group may be carried out by acylation under the action of the acid chloride or acid anhydride, sulfonylamine under the action of sulphonylchloride or sulfonic anhydride, alkilirovaniye be carried out by carbonylation, Allilueva, cyanidation, halogenation, amination, etc. when used as a transition metal catalyst such as a palladium catalyst; the transformation of the formyl group in a functional group may be carried out by alkylation or acylation under the action of a nucleophilic agent such as an ORGANOMETALLIC reagent or enolate.

The transformation of R4in a functional group in the intermediate derived ether 2-benzofuranol acid, obtained on the way In the process of getting a 6, can also be done using the same method, as shown in the diagram of the process of obtaining 7.

The processes of obtaining 1-7, shown above, are not intended to limit the methods of synthesis of compounds according to the invention, and any known in this field processes can also be used.

Derivatives benzofuran--Piron according to the invention and their salts obtained by the method described above, have the effect of inhibition of the biosynthesis of triglycerides, as well as the effect of reducing the amount of triglycerides in the blood and the effect of increasing the content of HDL in the blood, as demonstrated in the examples below, and sliimy below, if necessary, to obtain pharmaceutical compositions and to obtain inhibitors of the biosynthesis of triglycerides, agents that reduce triglycerides in the blood or agents that increase the amount of HDL in the blood, in accordance with the present invention.

The clinical application of the derived benzofuran--Piron according to the invention or salts thereof as an agent for the prophylaxis or treatment of hypertriglyceridemia, atherosclerosis and related diseases, it can be administered orally or parenterally, for example, vnutriuretrale, subcutaneously, intramuscularly, intravenously or transdermally, but preferred is oral or intravenous.

In the case of oral administration, the preparation may be in liquid or solid form. Solid dosage forms include tablets, pills, powders and granules. The active substance in such solid preparations mixed with pharmaceutically acceptable carriers, such as sodium bicarbonate, calcium carbonate, potato starch, saccharose, mannitol or carboxymethylcellulose. The composition may be manufactured in a conventional way, and other additives, for example, lubricants such as calcium stearate and magnesium stearate, may be settled by receipt of food coverage in the sputtering on the surface of the above-mentioned solid preparations, for example, an aqueous solution or a solution in an organic solvent substances that make up the food coating, such as phthalate cellulose acetate/ phthalate of hydroxypropylmethylcellulose, phthalate polyvinyl alcohol, a copolymer of styrene and maleic anhydride, or a copolymer of methacrylic acid or methyl methacrylate. Solid preparations such as powders or granules, can also be enclosed inside the capsules with food floor.

Liquid preparation for oral administration includes, for example, emulsifier, solution, suspension, syrup or elixir. Such drugs are commonly used pharmaceutically acceptable carriers, such as water or liquid petrolatum. As carriers are also used oil base, such as coconut oil, fractionated coconut oil, soybean oil or corn oil. Pharmaceutically acceptable carriers can also contain, if necessary, commonly used additives, flavorings, stabilizers or preservatives. The liquid preparation may be in the form of capsules formed from which people absorb guided substances, such as gelatin. Solid preparations for vnutribruchinnogo introduction include candles, prepared by known methods and with the CSOs aqueous or nonaqueous solution, suspension or emulsion. As pharmaceutically acceptable carriers non-aqueous solutions or suspensions may contain propylene glycol, polyethylene glycol, vegetable oil such as olive oil or soybean oil, or suitable for injectable organic ester, such as etiloleat. These preparations may also contain additives such as preservatives, humectants, emulsifiers, dispersing agents and stabilizers. These solutions, suspensions and emulsions can be sterilized by appropriate methods, such as filtration through a filter that retains bacteria, heat, adding a sterilizing agent, or ultraviolet radiation. After cooking and just before receiving sterile solid drug it can be dissolved in sterile water or sterile solution for injection. Fatty emulsion obtained by adding water to a homogeneous solution of the active ingredients in a vegetable oil such as soybean oil, and a phospholipid, such as lecithin, for use in injections can be homogenized using a homogenizer, such as jet homogenizer or an ultrasonic homogenizer.

Form the way.

When the active ingredient in accordance with the present invention is used as an agent for the treatment of hypertriglyceridemia or agent for the prevention of atherosclerosis, it can usually be administered in amounts from about 1 to 1000 mg per day for adults, although this dose depends on the patient's condition, age, sex, body mass index, and way of administration. This dose may be given as a single dose, or in several doses, for example, 2 to 6 doses per day.

Using the well-known pharmacological methods was determined by the efficiency of absorption of the active substance within the body for a specific physiologically active derivatives of benzofuran--Piron, on the basis of the various preferred route of administration.

Information confirming the possibility of carrying out the invention

Abbreviations used for all connections in the present description, including the examples, as well as groups within the structures of the compounds and the reagents are commonly used in the field of organic chemistry; the values of abbreviations is shown below.

THF: tetrahydrofuran, Et2O: diethyl ether, DMF: N,N-dimethylformamide, AcOEt: ethylamide), azodicarboxylic acid DMSO: dimethyl sulfoxide, Et3N: triethylamine, PY: pyridine, n-BuLi: n-utility, LDA: diisopropylamide lithium, AU2A: acetic anhydride, WSC: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, DCC: 1,3-dicyclohexylcarbodiimide, CDI: carbonyldiimidazole, HOBt: 1-hydroxybenzotriazole, PPTS: p-toluensulfonate pyridinium, TMSOTf: trimethylsilyltrifluoromethane, TfOH: triftoratsetata, Ms: methanesulfonyl, Tf: trifloromethyl, p-Ts: p-toluensulfonyl, Ph: phenyl, BU: butyl, Bzl: benzyl, AC: acetyl, TMS: trimethylsilyl.

Examples of making

Synthesis of intermediate products

Synthesis of methyl 2-benzophenoneoxymate

After the addition of thionyl chloride (3,80 ml) to a solution of 2-benzofuranol acid (2.00 g) in the Meon (60 ml) at -40oC, the mixture is stirred for 19 hours while the temperature is gradually increased to room. The reaction solution is concentrated under reduced pressure and the residue purified by column chromatography on silica gel (n-hexane/AcOEt=6/1) to obtain methyl 2-benzophenoneoxymate. Yield: 2.16 g (century 99,2%)

1H NMR ( ppm, D13): 3,99 (s, 3H), 7,28 to 7.50(m, 2H), 7,54 (s, 1H), 7,60(d, J=8,9 Hz, 1H), 7,69(d, J=7,6 Hz, 1H)

Synthesis of methyl 2-methyl-3-oxopentanoate

File) under cooling with ice. The reaction solution is stirred for 96 hours at room temperature and filtered through celite, then the mother liquid slowly concentrated under reduced pressure, and then distilled under reduced pressure to obtain methyl 2-methyl-3-oxopentanoate. Output: 105 g (century 94,8%)

1H NMR ( ppm, D13): 1,08 (t, J=7,3 Hz, 3H), of 1.35 (d, J=7,3 Hz, 3H), 2,45 to 2.72 (m, 2H), 3,54 (kV, J=7,3 Hz, 1H), of 3.73 (s, 3H)

Synthesis of methyl 3-exonerat

Pyridine (11.2 ml) and n-heptanoate (11.8 ml) are added to a solution merudorami acid (10.0 g) in CHCl2, (150 ml) at 0oC, the mixture was stirred at 0oC for 30 minutes and then at room temperature for 2 hours. The reaction solution is cooled to 0oWith add diluted hydrochloric acid and the extraction is carried out using a CH2CL2. The organic layer is washed with water and saturated brine, dried with Na2S04, and then filtered and concentrated. To the residue add Meon (150 ml) before heating under reflux for 3 hours. After cooling, the reaction solution was concentrated under reduced pressure and the residue purified by column chromatography on silica gel (n-hexane/AcOEt = 13/1)and obtain methyl 3-exonerat. Output: 8,51 g (century. 65 is), 3,74 (s, 3H)

Synthesis of methyl 2-methyl-3-exonerat

TO2CO3(2.67 g) are added to a solution of methyl 3-exonerat (3,01 g) and methyl iodide (2,77 g) in acetone (100 ml) and the mixture stirred at room temperature for 24 hours. The reaction solution is filtered through celite, then the mother liquid is concentrated under reduced pressure, the residue is purified by column chromatography on silica gel (n-hexane/AcOEt = 13/1) and get methyl 2-methyl-3-exonerat.

Output: 3.06 g (century 94.6%)

1H NMR ( ppm, D13): of 0.90 (t, J=6.9 Hz, 3H), from 1.21 to 1.39(m, N), from a rate of 1.51 to 1.65 (m, 2H), 2,47 to 2.56 (m, 2H), 3.53(q, J=7,3 Hz, 1H), of 3.73 (s, 3H)

Synthesis of ethyl 2-(benzyloxy)acetate

Benzyl alcohol (27.5 ml) are added to a suspension of NaH (1.1 g) in Et2O (250 ml) at 0oAfter stirring at 0oC for 10 minutes and at room temperature for 5 minutes, the reaction solution is cooled to a temperature of from -10 to 0oC and added dropwise to trichloroacetonitrile (27 ml) over 15 minutes. The reaction solution is stirred for one hour while the temperature is slowly increased to room temperature and then concentrated under reduced pressure. The solution Meon (1.0 ml) in n-pentane (100 ml) is added to the residue, the mixture vigorously of paramashiva shall concentrate here. To the residue add Et2O (80 ml), n-pentane (80 ml) and ethylglycol (25 g), then at 0oWith added TfOH (1.5 ml), after which the mixture was stirred at 0oWith 10 minutes and at room temperature for 2 hours. The reaction solution is filtered, the mother liquor was poured into a saturated aqueous solution of NaHCO3and the extraction is carried out with Et2O. the Organic layer is washed with water and dried over MgSO4, then filtered and concentrated. The residue is purified by column chromatography on silica gel (n-hexane/AcOEt=10/1-->6/1) and obtain ethyl 2-benzyloxyethyl.

Output: 38,76 g (century 83,2%)

1H NMR ( ppm, Dl3): of 1.29 (t, J=7,26 Hz, 3H), 4.09 to (s, 2H), 4,23 (kV, J=7,26 Hz, 2H), 4,63 (s, 2H), 7,21 to 7.45 (m, 5H)

Synthesis of methyl 6-benzyloxy-2,4-dimethyl-3,5-dioxopentanoate

A solution of methyl 2-methyl-3-oxopentanoate (of 13.05 g) in THF (100 ml) are added to a suspension of NaH (3.80 g) in THF (100 ml) at 0oAfter stirring at 0o15 minutes, add 1,63 M n-BuLi (58 ml) and the mixture was stirred at 0oWith 20 minutes to prepare dienoate light yellow color. The reaction solution is cooled to -78oC, add a solution of ethyl 2-(benzyloxy) acetate (17,56 g) in THF (30 ml), the mixture was stirred at -78oWith 5 minutes and then at 0oWith one t under neutral conditions. The organic layer was washed with saturated brine and dried with MgSO4, then filtered and concentrated. The residue is purified by column chromatography on silica gel (n-hexane/AcOEt= 5/1-->3/1) and obtain methyl 6-benzyloxy-2,4-dimethyl-3,5-dioxopentanoate. Output: 9,78 g (century. 37%)

1H NMR ( ppm, D13): from 1.17 to 1.42 (m, 6N), 3,62 up of 3.80 (m, 4H), 3,98 up to 4.28 (m, 3H), from 4.48 to 4.65 (m, 2H), 7.12 to 7.42 (m, 5H)

Synthesis of 4-atomic charges-6-(benzyloxy)methyl-3,5-dimethyl-2H-Piran-2-it

An aqueous solution (6 ml) of LiOH hydrate (64 mg) are added to a solution of methyl 6-benzyloxy-2,4-dimethyl-3,5-dioxopentanoate (430 mg) in THF (10 ml), the mixture is stirred at room temperature for 1.5 hours. The reaction solution is neutralized with diluted hydrochloric acid, after distillation of the volatile components under reduced pressure, the extraction is carried out with AcOEt at pH 3. The organic layer is dried with MgSO4then filter and concentrate. To the residue add AU2O (6 ml), after stirring at room temperature for 30 minutes, add pyridine (4 ml), the mixture is stirred at room temperature for one hour. The reaction solution is concentrated under reduced pressure and the residue purified by column chromatography on silicagel.7%)

1H NMR ( ppm, D13): of 1.88 (s, 3H), 1.93 and (s, 3H), of 2.34 (s, 3H), 4,35 (s, 2H), 4,58 (s, 2H), 7.23 percent to 7.41 (m, 5H)

Synthesis of 6-(benzyloxy )methyl-3,5-dimethyl-4-hydroxy-2H-Piran-2-it

TO2CO3(3.0 g) and water (10 ml) are added to a solution of 4-atomic charges-6-(benzyloxy)methyl-3,5-dimethyl-2H-Piran-2-it (between 6.08 g) in the Meon (100 ml), after stirring at room temperature overnight, the reaction solution is filtered through celite and the mother liquor concentrated under reduced pressure. To the residue water is added, the extraction is carried out with AcOEt, the organic layer is dried with Na2SO4, then filtered and concentrated. The residue is purified by column chromatography on silica gel (n-hexane/AcOEt= 5/1-->1/1) to obtain 6-(benzyloxy)methyl-3,5-dimethyl-4-hydroxy-2H-Piran-2-it. Output: 4,82 g (century. 86%) (TLC Rf=0.3; the hexane/t=1/1)

Synthesis of 6-(benzyloxy)methyl-3,5-dimethyl-4-methoxyethoxy-2H-Piran-2-it

Diisopropylethylamine (2.1 ml) are added to a solution of 6-(benzyloxy)methyl-3,5-dimethyl-4-hydroxy-2H-Piran-2-it (2,60 g) in THF (50 ml), after stirring the mixture at room temperature for one hour, added chloromethyl methyl ether (921 μl) at 0oC and the mixture is stirred at room temperature for one hour. After co is using AcOEt, the organic layer is dried with Na2SO4, then filtered and concentrated. The residue is purified by column chromatography on silica gel (n-hexane/AcOEt= 5/1-->1/1) and receive 6-(benzyloxy)methyl-3,5-dimethyl-4-methoxyethoxy-2H-Piran-2-it. Yield: 1.80 g (century. 60%) (TLC Rf=0,6; n-hexane/AcOEt=1/1)

Synthesis of 3,5-dimethyl-6-hydroxymethyl-4-methoxyethoxy-2H-Piran-2-it

20% Rd(OH)2/C (360 mg) are added to a solution of 6-(benzyloxy)methyl-3,5-dimethyl-4-methoxyethoxy-2H-Piran-2-it (1/80 g) in EtOH (50 ml), the mixture is vigorously stirred at room temperature for 3 hours in hydrogen atmosphere. The reaction solution is filtered through celite and the mother liquor concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (n-hexane/AcOEt=1/1) to obtain 3,5-dimethyl-6-hydroxymethyl-4-methoxyethoxy-2H-Piran-2-it. Yield: 1.26 g (century 99%) (TLC Rf=0,15; n-hexane/AcOEt=1/1)

Synthesis of 3,5-dimethyl-4-methoxyethoxy-6-(methylsulfonylamino)methyl-2H-Piran-2-it

The triethylamine (606 mg) are added to a solution of 3,5-dimethyl-6-hydroxymethyl-4-methoxyethoxy-2H-Piran-2-it (1.26 g) in THF (50 ml), after stirring the mixture at room temperature for one hour, add methanesulfonanilide (1,05 g) and the mixture was stirred at OEt, the organic layer is dried over Na2SO4, then filtered and concentrated. The residue is purified by column chromatography on silica gel (n-hexane/AcOEt=1/1) to obtain 3,5-dimethyl-4-methoxyethoxy-6-(methylsulfonylamino)methyl-2H-Piran-2-it. Yield: 1.35 g (century 73%) (TLC Rf= 0,5; n-hexane/AcOEt=1/1)

Synthesis of 6-bromomethyl-3,5-dimethyl-4-methoxyethoxy-2H-Piran-2-it

Sodium bromide (500 mg) are added to a solution of 3,5-dimethyl-4-methoxyethoxy-6-(methylsulfonylamino)methyl-2H-Piran-2-it (1.35 g) in DMF (20 ml), after stirring the mixture at room temperature for one hour, the reaction solution is concentrated under reduced pressure. Add to the residue water, the extraction is carried out with AcOEt, the organic layer dried over Na2SO4and then filtered and concentrated. The residue is purified by column chromatography on silica gel (n-hexane/AcOEt=1/1) to obtain 6-bromomethyl-3,5-dimethyl-4-methoxyethoxy-2H-Piran-2-it. Output: 1,21 g (century 99%) (TLC Rf=0,7; n-hexane/AcOEt=1/1)

Synthesis of methyl 6-hydroxybenzophenone-2-carboxylate

A suspension of 4-methoxysalicylaldehyde aldehyde (50 g), K2CO3(65 g) and methylpropanoate (65 g) in DMF (500 ml) was stirred at 60oC for one hour, after cooling, the reaction RA, the content of inorganic fillers layer is dried over MgSO4and then filtered and

concentrate. To the residue is added toluene (500 ml) with formation of a suspension and as you add DBU (70 g) and the mixture was stirred at 130oWith during the night. After cooling, the reaction solution was concentrated under reduced pressure, to the residue water is added and carry out the extraction with AcOEt. The organic layer is dried over MgSO4and then filtered and concentrated. The residue is dissolved in Meon (500 ml), add concentrated hydrochloric acid (50 ml) and the mixture was stirred at 60oWith during the night. After cooling, the reaction solution was concentrated under reduced pressure, to the residue add AcOEt (500 ml) and then slowly saturated aqueous solution Panso3(500 ml) to separate the organic and aqueous layers, the aqueous layer was extracted with AcOEt. The organic layer is dried over MgSO4, then filtered and concentrated. The residue is dissolved in CH2Cl2(1000 ml), then slowly add tribromide boron (125 g) at 0oC, then the mixture is stirred at room temperature for 24 hours. The reaction solution is concentrated under reduced pressure and the resulting brown oil was dissolved in Meon (500 ml) is their night. After cooling, the reaction solution was concentrated under reduced pressure, to the residue add AcOEt (500 ml) and then slowly add saturated aqueous solution Panso3(500 ml) to separate the organic and aqueous layers, the aqueous layer was extracted with AcOEt. The organic layer is dried over MgSO4then filter and concentrate.

The residue is purified by column chromatography on silica gel (n-hexane/AcOEt= 3/1) to give methyl 6-hydroxybenzophenone-2-carboxylate. Output: of 37.9 g (century. 60%)

1H NMR ( ppm, Dl3): 3,88 (s, 3H), from 5.50 to 6.50 (broadened, 1H), 6,80 to 7.80(m, 4H)

Synthesis of methyl 6-(benzyloxy)benzofuran-2-carboxylate

A solution of methyl 6-hydroxybenzophenone-2-carboxylate (3.58 g) in THF (30 ml) is added slowly to a suspension of NaH (800 mg) in THF (100 ml) at room temperature, after stirring for one hour, add DMF (35 ml) and then slowly add benzylbromide (3.77 g) and the mixture is stirred for one hour. To the reaction solution was added water, carry out the extraction with AcOEt, the organic layer is dried with MgSO4, then filtered and concentrated. The residue is purified by column chromatography on silica gel (n-hexane/AcOEt=10/1) to the floor, N), 5,19 (s, 2H), 6,85 (DD, J=8,1 Hz, 2.0 Hz, 1H), 7,05 (d, J=2.0 Hz, 1H), 7,43 (s, 1H), 7,51(d, J=8,1 Hz, 1H)

Synthesis of 2-hydroxy-4-martinbaselierit

After slow addition of a solution of 3-morpholinopropan (5.0 g) in THF (100 ml) to 3 M solution in diethyl ether (10 ml) ethylacetamide, the mixture was stirred at 30oC for 1.5 hours. Add paraformaldehyde (3.0 g) and Et3N (3.0 g) to the reaction solution and the mixture was stirred at 80oWith 4 hours. After cooling, add 6 N aqueous solution of hydrochloric acid (20 ml), the mixture is stirred for one hour, then the organic and aqueous layers are separated and the aqueous layer was alkalinized with a weak alkali prior to extraction with AcOEt. The organic layers are combined and dried with MgSO4, then filtered and concentrated. The residue is purified by column chromatography on silica gel (n-hexane/AcOEt=3/1) to obtain 2-hydroxy-4-martinbaselierit. Output: 3.57 g (century. 62%)

1H NMR ( ppm, D13): 3,30 (t, J=4.8 Hz, 4H), of 3.84 (t, J=4, 8 Hz, 4H), 6,18 (d, J=2.1 Hz, 1H), 6,55 (DD, J=8,9 Hz and 2.1 Hz, 1H), 7,78 (d, J=8,9 Hz, 1H), 10.30 a.m. (s, 1H)

Synthesis of methyl 6-morpholinopropan-2-carboxylate

Methylbromide (3.0 g) and K2CO3(3.0 g) are added to a solution of 2-hydroxy-4-morpholinosydnonimine (3.5 g) in the Ute and the mother liquid is concentrated under reduced pressure. To the residue add Meon (100 ml) and concentrated hydrochloric acid (10 ml), after heating under reflux for 5 hours, the reaction solution is concentrated under reduced pressure. To the residue is added saturated aqueous solution Panso3(100 ml) before extraction with AcOEt and the organic layer is dried with MgSO4, then filtered and concentrated. The residue is purified by column chromatography on silica gel (n-hexane/AcOEt=5/1) to obtain methyl 6-morpholinopropan-2-carboxylate. Yield: 3.1 g (century 71%)

1H NMR ( ppm, Dl3): 3,22 (t, J=4.8 Hz, 4H), 3,80 (t, J=4.8 Hz, 4H), 3.95(s, 3H), of 6.96 7.00(m, 2H), 7,44 (s, 1H), 7,53 (d, J=8.6 Hz, 1H)

Synthesis of methyl 5-formylbenzoate-2-carboxylate

TO2CO3(30 g) are added to a solution of 5-formelsammlung aldehyde (25 g) and methylpropanoate (30 g) in acetonitrile (500 ml), after heating under reflux for 24 hours and then cooled, the reaction solution is filtered and the mother liquor concentrated under reduced pressure. Before extraction with AcOEt to the residue add saturated aqueous solution of ammonium chloride (100 ml), the organic layer is dried over MgSO4and then filtered and concentrated. The residue is purified with PD: 15 g (century. 44%)

Mass spectrum: [M++ N] = 205,2

Synthesis of methyl 5-(dimethoxymethyl)benzofuran-2-carboxylate

Meteorophobia (1.0 g) and associated with the polymer PPTS (1.0 g) are added to a solution of methyl 5-formylbenzoate-2-carboxylate (15 g) in Meon (100 ml), after the mixture is allowed to stand at room temperature for 8 hours, the reaction solution is filtered and the mother liquor concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (n-hexane/AcOEt = 9/1) to obtain methyl 5-(dimethoxymethyl)benzofuran-2-carboxylate. Yield: 10 g (C. 54%)

1H NMR ( ppm, Dl3): at 3.35 (s, 3H), 3,98 (s, 3H), 5,49 (s, 1H), 7,53 up to 7.61 (m, 3H), 7,81 (s, 1H)

The following connection receive in a manner analogous to that described in the previous example, by the method well known to experts in the field of organic chemistry.

Ethyl 5-bromobenzophenone-2-carboxylate

1H NMR ( ppm, Dl3): USD 1.43 (t, J=7,3 Hz, 3H), of 4.45 (q, J=7,3 Hz, 2H), 7,45 (s, 1H), 7,47 (d, J=8,4 Hz, 1H), 7,54(DD, J=8,4 Hz, 2.2 Hz, 1H), 7,82 (d, J=2.2 Hz, 1H)

Example 1. Synthesis of 4-atomic charges-6(benzofuran-2-yl)-3,5-dimethyl-2H-Piran-2-it

After adding 60% NaH (220 mg) to a solution of methyl 2-methyl-3-oxopentanoate (750 mg) in THF (5 ml) at 0oC and stirring at 0oWith TES stirred at -78oWith 30 minutes to cook Dienst. Add a solution of methyl 2-benzophenoneoxymate (300 mg) in THF (10 ml) to dienoate, the mixture was stirred at -78oWith 20 minutes. The reaction solution allowed to warm to 0oTo add to extinguish the aqueous solution of KHSO4carry out the extraction with AcOEt. The organic layer was washed with saturated brine and dried over MgSO4, then filtered and concentrated. The residue is purified by column chromatography on silica gel (n-hexane/AcOEt= 3/1-->2/1) to give the crude methyl 5-(benzofuran-2-yl)-2,4-dimethyl-3,5-dioxopentanoate. Output: 433 mg (mix)

An aqueous solution (30 ml) of LiOH hydrate (2,62 g) are added to a solution of 5-(benzofuran-2-yl)-2,4-dimethyl-3,5-dioxopentanoate (14,98 g) in the Meon (50 ml), after stirring at room temperature for 20 minutes, Meon distilled off under reduced pressure. An aqueous solution of the residue is washed with Et2O, then cooled with ice and add an aqueous solution of KHSO4to bring the pH value to the range from 2.0 to 2.5. Precipitated precipitated crystals are filtered and washed with water. Mother liquor is saturated with brine and extracted with AcOEt and the organic layer concentrated. The residue is combined with the filtered kristenye 3.5 hours. The reaction solution is concentrated under reduced pressure and the residue is recrystallized from n-hexane/AcOEt=3/1 with getting 4 atomic charges-6-(benzofuran-2-yl)-3,5-dimethyl-2H-Piran-2-it. Output: 6.11 g (century 47,3%)

1H NMR ( ppm, Dl3): 2,00 (s, 3H), 2,31 (s, 3H), 2.40 a (s, 3H), 7.23 percent to 7.42 (m, 2H), was 7.36 (s, 1H), 7,53 (d, J=8,2 Hz, 1H), 7,65 (d, J=7,6 Hz, 1H)

Example 2. Synthesis of 6-(benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-it

An aqueous solution (30 ml) of LiOH hydrate (465 mg) are added to a solution of 4-atomic charges-6-(benzofuran-2-yl)-3,5-dimethyl-2H-Piran-2-she (3.00 g) in the Meon (100 ml) at 0oAfter stirring at room temperature for 2 hours, the Meon distilled off under reduced pressure. The residue is washed with Et2O, then add aqueous solution of KHSO4at 0oTo obtain a pH of 2.0. Precipitated precipitated crystals are filtered off and thoroughly washed with water and Et2O in that order and then dried to obtain 6-(benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-it. Output: 2,54 g (century 98.5%)

1H NMR ( ppm, DMSO-d6): of 1.93 (s, 3H), of 2.28 (s, 3H), 7,28 to 7.47 (m, 2H), 7,39 (s, 1H), 7,68 (d, J=8,3 Hz, 1H), 7,74 (d, J=7,3 Hz, 1H), 10,91 (broad s, 1H)

Example 3. Synthesis of 6-(benzofuran-2-yl)-4-benzoyloxy-3,5-dimethyl-2H-Piran-2-it

Pyridine (64 ml) and benzoyl chloride (45 memes stirred at room temperature for 50 minutes. The reaction solution was poured into an aqueous solution of KHSO4and extracted with AcOEt, the organic layer was washed with saturated brine and dried over MgSO4, then filtered and concentrated. The residue is purified by column chromatography on silica gel (n-hexane/AcOEt= 5/1-->4/1) then get 6-(benzofuran-2-yl)-4-benzoyloxy-3,5-dimethyl-2H-Piran-2-it. Yield: 48 mg (century 71,2%) Crystals are light yellow in color.

1H NMR ( ppm, Dl3): 2,04 (s, 3H), of 2.35 (s, 3H), 7,24 to 7.42 (m, 3H), 7,49 up to 7.77 (m, 5H), 8,23 (d, J=7,3 Hz, 2H)

Example 4. Synthesis of 6-(benzofuran-2-yl)-3,5-dimethyl-4-methanesulfonate-2H-Piran-2-it

Et3N (130 μl) and methanesulfonamide (24 μl) are added to a suspension of 6-(benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-it (40 mg) in THF (5 ml)/ the mixture is stirred at room temperature for one hour. The reaction solution was poured into an aqueous solution of KHSO4and extracted with AcOEt, the organic layer was washed with saturated brine and dried over MgSO4, then filtered and concentrated. The residue is purified by column chromatography on silica gel (n-hexane/AcOEt= 2/1), and then get 6-(benzofuran-2-yl)-3,5-dimethyl-4-methanesulfonate-2H-Piran-2-it. Yield: 46 mg (century 88,2%) Yellow crystals.


Example 5. Synthesis of 6-(benzofuran-2-yl)-3,5-dimethyl-4-(2-pyridylcarbonyl)-2H-Piran-2-it

WSC (43 mg) are added to a solution of 6-(benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-it (40 mg), pikolinos acid (23 mg) and HOBt (21 mg) in DMF (3 ml), the mixture is stirred at room temperature for a period of 21.5 hours. The reaction solution is concentrated under reduced pressure, the residue is purified by column chromatography on silica gel (n-hexane/AcOEt= 2/1-->3/2), then get 6-(benzofuran-2-yl)-3,5-dimethyl-4-(2-pyridylcarbonyl)-2H-Piran-2-it.

Yield: 30 mg (century 53.2%) Crystals are light yellow in color.

1H NMR ( ppm, Dl3): 2,07 (s, 3H), of 2.38 (s, 3H), 7,25 to 7.42 (m, 3H), 7,53 (d, J= 8,2 Hz, 1H), up to 7.61 of 7.69(m, 2H), to 7.99 (DD, J=1.6 Hz, 7.9 Hz, 1H), 8,32 (d, J=7.9 Hz, 1H), 8,90 (d, J=4,6 Hz, 1H)

Example 6. Synthesis of 3,5-dimethyl-4-hydroxy-6(6-morpholinopropan-2-yl)-2H-Piran-2-it.

A solution of methyl 2-methyl-3-oxopentanoate (865 mg) in THF (30 ml) is added slowly to a suspension of NaH (240 mg) in THF (50 ml), after stirring for 10 minutes, the mixture is cooled to -78oWith and slowly add (dropwise) was 1.58 M n-BuLi (3.8 ml). After stirring the reaction solution at -78oC for 30 minutes, slowly add a solution of methyl 6-morpholinopropan-2-carboxylate the aqueous solution of ammonium chloride (30 ml), after bringing it to room temperature, the extraction is carried out AcOEt, the organic layer is dried over MgSO4filter and concentrate. The residue is dissolved in Meon (30 ml) and THF (30 ml), add 4 N aqueous solution of lithium hydroxide (10 ml), after stirring at room temperature for 4 hours, slowly add saturated aqueous solution of KHSO4(50 ml). Fallen yellow precipitate is filtered off and washed with AcOEt, and then receive 3,5-dimethyl-4-hydroxy-6-(6-morpholinopropan-2-yl)-2H-Piran-2 he. Yield: 1.40 g (century. 82%)

1H NMR ( ppm, DMSO-d6): 1,92 (s, 3H), and 2.26 (s, 3H), 3,19 (t, J=4.8 Hz, 4H), of 3.75 (t, J=4.8 Hz, 4H), 7,05 (d, J=8,4 Hz, 1H), 7,16 (s, 1H), 7,25 (s, 1H), 7,54 (d, J=8,4 Hz, 1H), and 10.8 (s, 1H)

Example 7. Synthesis of 3,5-dimethyl-6-(5-formylbenzoate-2-yl)-4-hydroxy-2H-Piran-2-it

A solution of methyl 2-methyl-3-oxopentanoate (7.5 g) in THF (50 ml) is added slowly to a suspension of NaH (2.1 g) in THF (200 ml), after stirring for 10 minutes, the mixture is cooled to -78oC and slowly added dropwise 1,58 M n-BuLi (32 ml). After stirring the reaction solution at -78oC for 30 minutes, a solution of methyl 5-(dimethoxymethyl)benzofuran-2-carboxylate (10 g) in THF (50 ml) is added slowly and the mixture was stirred at -78oWith 4 hours. To the reaction solution was added Nassau AcOEt, the organic layer is dried over MgSO4, then filtered and concentrated. The residue is dissolved in Meon (100 ml) and THF (100 ml), add 4 N aqueous solution of lithium hydroxide (25 ml), after stirring at room temperature for 4 hours, slowly add saturated aqueous solution of KHSO4(50 ml). Fallen yellow precipitate is filtered off and washed with AcOEt, and then receive 3,5-dimethyl-6-(5-formylbenzoate-2-yl)-4-hydroxy-2H-Piran-2-it.

Yield: 10.8 g (century. 95%)

1H NMR ( ppm, DMSO-d6): to 1.87 (s, 3H), of 2.23 (s, 3H), 7,51 (s, 1H), 7,78 to a 7.92 (m, 2H), 8,28 (s, 1H), 10.0 g (s, 1H)

Example 8. Synthesis of 4-atomic charges-3,5-dimethyl-6-(5-formylbenzoate-2-yl)-2H-Piran-2-it

After addition of Et3N (1.7 g) to a suspension of 3,5-dimethyl-6-(5-formylbenzoate-2-yl)-4-hydroxy-2H-Piran-2-she (5.0 g) in CH2CL2(100 ml), the mixture is cooled with ice, add acetylchloride (1,32 g) and the mixture is stirred at room temperature for one hour.

To the reaction solution was added water (100 ml) and the extraction is carried out AcOEt, the organic layer is dried over MgSO4, then filtered and concentrated. The residue is purified by column chromatography on silica gel (n-hexane/AcOEt= 3/1) then get 4 atomic charges-3,5-dimethyl-6-(5-for,46 (s, 1H), 7,66 (d, J=8,4 Hz, 1H), of 7.96 (d, J=8,4 Hz, 1H), to 8.20 (s, 1H), 10,1 (s, 1H)

Example 9. Synthesis of 3,5-dimethyl-6(5-((3,5-dioxo-2,4-thiazolidinedione)methyl)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he

Piperidine (100 mg) are added to a solution of 4-atomic charges-3,5-dimethyl-6-(5-formylbenzoate-2-yl)-2H-Piran-2-it (374 mg) and 1,3-thiazolidin-2,4-dione (135 mg) in THF (50 ml), the mixture is subjected to reflux for 4 hours. After cooling, to the reaction solution was added 15% aqueous sodium hydroxide solution (10 ml), after stirring for one hour, concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (CH2Cl2/MeOH=5/1), and then receive 3,5-dimethyl-6-(5-((3,5-dioxo-2,4-thiazolidinedione)methyl)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-it. Yield: 400 mg (century 91%)

1H NMR ( ppm, DMSO-d6): 1,96 (s, 3H), 2,22 (s, 3H), 7,32 (s, 1H), 7,45 (d, J=8,4 Hz, 1H), of 7.75 (d, J=8,4 Hz, 1H), 8,12 (s, 1H), 8,24 (s, 1H), 10,91 (c, 1H), 12,90 (c, 1H)

Example 10. Synthesis of 3,5-dimethyl-6-(5-((3,5-dioxo-2,4-thiazolidine)methyl)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-it

To 3,5-dimethyl-6-(5-((3,5-dioxo-2,4-thiazolidinedione)methyl)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-ONU (350 mg) in a mixed solvent consisting of EtOH (10 ml) and 1,4-dioxane (10 ml) is added 10% Rd/C (70 mg), the mixture shall irout under reduced pressure, then the residue purified by column chromatography on silica gel (CH2CL2/Meon=5/1), and then receive 3,5-dimethyl-6-(5-((3,5-dioxo-2,4-thiazolidine)methyl)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-it. Output: 352 mg (yield quantitative)

1H NMR ( ppm, DMSO-d6): 1,97 (s, 3H), 2,24 (s, 3H), 3,34 to 3,55 (m, 1H), 3,67 to 3,82 (m, 1H), 4,98 to 5.01 (m, 1H), 7,24 (s, 1H), 7,39 (d, J= 8,4 Hz, 1H), to 7.61 (d, J=8,4 Hz, 1H), 8,12 (s, 1H), of 10.93 (s, 1H), 12,20 (s, 1H)

Example 11. Synthesis of (6-benzofuran-2-yl)-4-hydroxy-3-methyl-5-n-pentyl-2H-Piran-2-it

A solution of methyl 2-methyl-3-exonerat (a 3.06 g) in THF (5 ml) are added to a suspension of 60% NaH (608 mg) in THF (30 ml) while cooling with ice and the mixture was stirred at 0oC for 10 minutes and then at room temperature for 30 minutes. The reaction solution is cooled to -78oTo add 1,66 M n-BuLi (9,2 ml), the mixture was stirred at -78oWith 30 minutes to get Dienst. A solution of methyl 2-benzophenoneoxymate (1.25 g) in THF (5 ml) are added to dienoate, the mixture was stirred at -78oWith 30 minutes. The reaction solution is brought to a temperature of 0oTo add an aqueous solution of NH4Cl for clearing, followed by the extraction with AcOEt. The organic layer is washed with water and saturated brine in this order, Satania 2N LiOH (30 ml) and stirring at room temperature for 2 hours, add 1N HCl at 0oFor acidification to approximately pH 3 and the extraction is carried out AcOEt. The organic layer is washed with water and saturated brine in this order, then dried with Na2SO4filter and concentrate. Pyridine (20 ml) and AU2O (20 ml) is added to the residue, after stirring the mixture at room temperature for 5 hours, it concentrated under reduced pressure. The residue is dissolved in Meon (20 ml), add imidazole (483 mg) at 0oAfter stirring the mixture at 0oC for 10 minutes and then at room temperature for 30 minutes she concentrated under reduced pressure. To the residue add AcOEt and loose precipitated crystals are filtered out. The crystals are recrystallized from EtOH, then get 6-(benzofuran-2-yl)-4-hydroxy-3-methyl-5-n-pentyl-2H-Piran-2-it.

Output: 357,9 mg (century 16,1%)

1H NMR ( ppm, DMSO-d6): of 0.87 (t, J=6.9 Hz, 3H), from 1,28 to 1.60 (m, 6N), of 1.93 (s, 3H), 2,74 to 2.85 (m, 2H), 7,28 to 7.46 (m, 3H), 7,63 (d, J=8,3 Hz, 1H), of 7.75 (d, J=7,3 Hz, 1H), 10,86 (broad s, 1H)

Example 12. Synthesis of 3,5-dimethyl-4-hydroxy-6-(5-methoxybenzophenone-2-yl)-2H-Piran-2-it

TO2CO3(138 mg) are added to a solution of 5-methoxysalicylaldehyde aldehyde (152 mg) and 6-methyl bromide-3,5-dimethyl-4-methoxyethoxy-2N-p is a solution of hydrochloric acid to the reaction solution, after stirring for one hour, the extraction is carried out AcOEt, after which the organic layer is dried over MgSO4, then filtered and concentrated. The residue is purified by column chromatography on silica gel (n-hexane/AcOEt= 1/1)/ then receive 3,5-dimethyl-4-hydroxy-6-(5-methoxybenzophenone-2-yl)-2H-Piran-2-it. Output: 229 mg (century 80%)

1H NMR ( ppm, Dl3): a 2.01 (s, 3H), of 2.25 (s, 3H), of 4.00 (s, 3H), from 5.50 to 6.50 (broad s, 1H), 6,80 to 7.80(m, 4H)

Example 13. Synthesis of 3,5-dimethyl-4-hydroxy-6-(7-methoxybenzophenone-2-yl)-2H-Piran-2-it

3,5-dimethyl-4-hydroxy-6-(7-methoxybenzophenone-2-yl)-2H-Piran-2-he will get according to methodology described in the previous example.

Yield: 78%

1H NMR ( ppm, Dl3): 2,10 (s, 3H), and 2.26 (s, 3H), of 4.00 (s, 3H), from 5.50 to 6.50 (broad s, 1H), 6,80 to 7.80 (m, 4H)

Example 14. Synthesis of 6-(5-aminobenzophenone-2-yl)-3,5-dimethyl-4-methoxyethoxy-2 N-Piran-2-she and 3,5-dimethyl-6-(5-(ethylamino)benzofuran-2-yl)-4-methoxyethoxy-2H-Piran-2-it

To a solution of 3,5-dimethyl-4-methoxyethoxy-6-(5-nitrobenzophenone-2-yl)-2H-Piran-2-it (100 mg) in dioxane (20 ml) and EtOH (20 ml) add 5% Rd/C (5 mg), after saturation of the reaction vessel with hydrogen, the mixture is stirred at room temperature overnight. The reaction solution is filtered and the end is up 6-(5-aminobenzophenone-2-yl)-3,5-dimethyl-4-methoxyethoxy-2H-Piran-2-he and 3,5-dimethyl-6-(5-(ethylamino)benzofuran-2-yl)-4-methoxyethoxy-2H-Piran-2-it.

6-(5-aminobenzophenone-2-yl)-3,5-dimethyl-4-methoxyethoxy-2H-Piran-2-he;

Yield: 45 mg (century. 49%)

1H NMR ( ppm, Dl3): 2,12 (s, 3H), 2.42 (s, 3H), of 3.64 (s, 3H), 5,16 (s, 2H), 6,83 (DD, J=2.3 Hz, a 8.9 Hz, 1H), of 6.96 (d, J=2.3 Hz, 1H), 7,20 (s, 1H), 7,33 (d, J=8,9 Hz, 1H), 7,42 (2N)

3,5-dimethyl-6-(5-(ethylamino)benzofuran-2-yl)-4-methoxyethoxy-2H-Piran-2-he;

Yield: 33 mg (B. 33%)

1H NMR ( ppm, Dl3): of 1.30 (t, J=7,3 Hz, 3H), 2,11 (s, 3H), 2,39 (s, 3H), 3,19 (kV, J=7,3 Hz, 2H), 3,62 (s, 3H), 5,11 (s, 2H), 6,69 (DD, J=2.3 Hz, a 8.9 Hz, 1H), 6.75 in (d, J=2.3 Hz, 1H), 7,20 (s, 1H), 7,31 (d, J=8,9 Hz, 1H)< / BR>
Example 15. Synthesis of 6-(5-(acetylamino)benzofuran-2-yl)-3,5-dimethyl-4-methoxyethoxy-2H-Piran-2-it

Pyridine (400 μl) and AU20 (15 µl) was added to 6-(5-aminobenzophenone-2-yl)-3,5-dimethyl-4-methoxyethoxy-2H-Piran-2-ONU (45 mg), after stirring the mixture at room temperature for 6 hours, add an aqueous solution of NH4Cl and the extraction is carried out using a CH2CL2. The organic layer is dried, filtered and concentrated, the residue is purified by thin layer chromatography on silica gel (CH2Cl2) then get 6-(5-acetylamino)benzofuran-2-yl)-3,5-dimethyl-4-methoxyethoxy-2H-Piran-2-it. Yield: 20 mg (B. 39%)

1H NMR ( ppm, Dl3): 2,10 (s, 3H), 2,17 (s, 3H), 2,43 (s, 3H), of 3.64 (s, 3H), 5,20 (s, 2H), 7,32 (s, 1H), and-2H-Piran-2-it

Add THF (20 ml) to 6-(5-aminobenzophenone-2-yl)-3,5-dimethyl-4-methoxyethoxy-2H-Piran-2-ONU (58 mg) and stirred, then add one drop of concentrated hydrochloric acid and the mixture is stirred at room temperature for one hour. The reaction solution is concentrated under reduced pressure and the residue purified by thin layer chromatography on silica gel (n-hexane/AcOEt = 1/1), and then obtain 6-(5-aminobenzophenone-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-it. Yield: 13 mg (B. 27%)

1H NMR ( ppm, DMSO-d6): of 1.93 (s, 3H), and 2.27 (3H), of 6.71 (DD, J=2.0 Hz, a 8.9 Hz, 1H), 6,79 (d, J=2.0 Hz, 1H), 7,16 (s, 1H), 7,33 (d, J=8,9 Hz, 1H)

Example 17. Synthesis of 6-(6-(benzyloxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-she and 4 atomic charges-6-(6-benzyloxy)benzofuran-2-yl)-3,5-dimethyl-2H-Piran-2-it

A solution of methyl 2-methyl-3-oxopentanoate (3,24 g) in THF (30 ml) is added slowly to a suspension of NaH (900 mg) in THF (50 ml) at 0oAfter stirring for 10 minutes, cooled to -78oC and slowly added dropwise 1,58 M n-BuLi (14,2 ml). After stirring the reaction solution at -78oC for 30 minutes, slowly add a solution of methyl 6-(benzyloxy)benzofuran-2-carboxylate (4.26 deaths g) in THF (15 ml) and the mixture was stirred at -78oC for 4 hours the reaction mass to room, the extraction is carried out with AcOEt, the organic layer dried over Na2SO4, then filtered and concentrated. The residue is dissolved in Meon (30 ml) and THF (10 ml), add 4 N aqueous solution of lithium hydroxide (5 ml) and water (50 ml), after stirring at room temperature for 4 hours, then slowly add saturated aqueous solution of KHSO4(30 ml). Fallen yellow precipitate is filtered off and washed with AcOEt to obtain 6-(6-(benzyloxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-it. Output: 964 mg (B. 25%)

1H NMR ( ppm, DMSO-d6): 2,00 (s, 3H), 2,24 (s, 3H), at 5.27 (s, 2H), 7,11 (d, J=a total of 8.74 Hz, 1H), 7,30 to 7.70(m, 8H), and 10.8 (broad s, 1H)

After that, the filtrate is concentrated under reduced pressure, add water (30 ml) and AcOEt (30 ml), the organic and aqueous layers separated, the aqueous layer was extracted with AcOEt. The organic layers are combined, dried over MgSO4filter and concentrate. To the residue add acetic anhydride (10 ml) and pyridine (3 ml), after stirring overnight, the reaction solution is concentrated under reduced pressure and purified by column chromatography on silica gel (n-hexane/AcOEt=5/1-->1/1) to obtain 4-atomic charges-6-(6-(benzyloxy)benzofuran-2-yl)-3,5-dimethyl-2H-Piran-2-on 7,80 (m, N)

Example 18. Synthesis of 4-atomic charges-3,5-dimethyl-6-(6-hydroxybenzophenone-2-yl)-2H-Piran-2-it

To a solution of 4-atomic charges-6-(6-(benzyloxy)benzofuran-2-yl)-3,5-dimethyl-2H-Piran-2-she (500 mg) in EtOH (50 ml) and 1,4-dioxane (50 ml) is added 10% Pd/C (100 mg), the mixture is vigorously stirred at room temperature for 3 hours in hydrogen atmosphere. The reaction solution is filtered through celite, then the filtrate concentrated under reduced pressure and the residue purified by column chromatography on silica gel (n-hexane/AcOEt=1/1) to obtain 4-atomic charges-3,5-dimethyl-6-(6-hydroxybenzophenone-2-yl)-2H-Piran-2-it. Output: 388 mg (century. 95%)

1H NMR ( ppm, Dl3): of 1.92 (s, 3H), of 1.97 (s, 3H), is 2.37 (s, 3H), from 5.50 to 6.50(broad s, 1H), 6,80 to 7.80(m, 4H).

Example 19. Synthesis of 4-atomic charges-3,5-dimethyl-6-(6-(tripterocalyx)benzofuran-2-yl-2H-Piran-2-he

Add pyridine (100 mg) to a solution of 4-atomic charges-3,5-dimethyl-6-(6-hydroxybenzophenone-2-yl)-2H-Piran-2-it (385 mg) in CH2CL2(10 ml), after stirring at room temperature for one hour and slowly add triftormetilfullerenov (415 mg) under ice cooling, the mixture is stirred at room temperature for 2 hours. A saturated aqueous solution Panso3SO4, then filtered and concentrated. The residue is purified by column chromatography on silica gel (n-hexane/AcOEt=2/1) to obtain 4-atomic charges-3,5-dimethyl-6-(6-(tripterocalyx)benzofuran-2-yl)-2H-Piran-2-it. Output: 392 mg (century. 72%) Mass analysis: [M++ N] = 447,3

Example 20. Synthesis of 4-atomic charges-3,5-dimethyl-6-(6-methoxycarbonyl)benzofuran-2-yl)-2H-Piran-2-it

After adding a solution of 4-atomic charges-3,5-dimethyl-6-(6-(tripterocalyx)benzofuran-2-yl)-2H-Piran-2-she (350 mg) in THF (5 ml) and Et3N (80 mg) in a mixed solution of palladium acetate (3.5 mg) and diphenylphosphane (6.5 mg) in DMSO (5 ml) and Meon (5 ml), the mixture is stirred at room temperature for one hour in an atmosphere of carbon monoxide, then additionally stirred at 80oWith 2 hours. The reaction solution is concentrated under reduced pressure and the residue purified by column chromatography on silica gel (n-hexane/AcOEt = 1/1) to obtain 4-atomic charges-3,5-dimethyl-6-(6-(methoxycarbonyl)benzofuran-2-yl)-2H-Piran-2-it.

Yield: 92 mg (B. 33%)

Mass analysis: [M++ N] = 357,3

Example 21. Synthesis of 6-(6-carboxybenzene-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-it

A mixed solution of 4-atomic charges-3,5-dimethyl-6-(is remediat at room temperature for one hour, then the reaction solution is acidified with aqueous 1N hydrochloric acid and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (AcOEt/MeOH=5/1) to obtain 6-(6-carboxybenzene-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-it. Yield: 71 mg (yield quantitative) Mass analysis: [M++ N] = 301,2

Example 22. Synthesis of 3,5-dimethyl-4-hydroxy-6-(6-(methoxycarbonyl)benzofuran-2-yl)-2H-Piran-2-it

Trimethylsilyldiazomethane (2 M hexane solution, 85 μl) are added to a mixed solution of 6-(6-carboxybenzene-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-it (50 mg) in Meon (5 ml) and toluene (1 ml), the mixture is stirred at room temperature for 10 minutes. After adding to the reaction solution of acetic acid to absorb excess trimethylsilyldiazomethane perform its concentration under reduced pressure. The residue is purified by column chromatography on silica gel (CH2Cl2/MeOH = 9/1) to obtain 3,5-dimethyl-4-hydroxy-6-(6-(methoxycarbonyl)benzofuran-2-yl)-2H-Piran-2-it.

Yield: 50 mg (century 96%)

Mass analysis[M++ N] = 315,3

Example 23. Synthesis of 4-atomic charges-3,5-dimethyl-6-(6-dimethylaminobenzophenone-2-yl)-2H-Piran-2-it

Tetrakis-6-(6-(tripterocalyx)benzo-furan-2-yl)-2H-Piran-2-she (45 mg) in toluene (5 ml), the mixture was stirred at 50oWith during the night. After cooling, the reaction solution was concentrated under reduced pressure, the residue is purified by column chromatography on silica gel (n-hexane/AcOEt=5/1) to obtain 4-atomic charges-3,5-dimethyl-6-(6-dimethylaminobenzophenone-2-yl)-2H-Piran-2-it. Output: 9.6 mg (B. 28%) Mass analysis: [M++ N] = 342,3

Example 24. Synthesis of 4-atomic charges-3,5-dimethyl-6-(6-(2-furyl)benzofuran-2-yl)-2H-Piran-2-it

4 atomic charges-3,5-dimethyl-6-(6-(2-furyl)benzofuran-2-yl)-2H-Piran-2-he will get according to the method similar to the method of the previous example, using 2-(tributylstannyl)furan.

Yield: 31 mg (century 87%)

Mass analysis: [M++ N] = 365,3

Example 25. Synthesis of 4-atomic charges-3,5-dimethyl-6-(6-(2-thienyl)benzofuran-2-yl)-2H-Piran-2-it

4 atomic charges-3,5-dimethyl-6-(6-(2-thienyl)benzofuran-2-yl)-2H-Piran-2-he will get according to the method similar to the method of the previous example, using 2-(tributylstannyl)thiophene Yield: 31 mg (century 85o%) Mass analysis: [M++ N ] = 381,4

Example 26. Synthesis of 3,5-dimethyl-4-hydroxy-6-(6-methoxybenzophenone-2-yl)-2H-Piran-2-it

TO2CO3(1,38 g) are added to a solution of 4-methoxysalicylaldehyde aldehyde (1.52 g) and 6-bromo-3,5-dimethyl-4-methoxyethoxy-2H-Piran-2-it (2,77 g) in DMF (50 lannom pressure. To the residue water is added (50 ml), the extraction is carried out with AcOEt, the organic layer is dried over MgSO4filter and concentrate. The residue is purified by column chromatography on silica gel (n-hexane/AcOEt=1/1) to obtain of 3.46 g of yellow oil. Add diisopropylethylamine (1.29 g) and DMF (20 ml) of 1.74 g of yellow oil, previously heated under reflux overnight. After cooling slowly add 6 N aqueous solution of hydrochloric acid (10 ml) to the reaction solution, the mixture is stirred at room temperature for one hour, then concentrated under reduced pressure. To the residue water is added (50 ml), the extraction is carried out with AcOEt, the organic layer is dried over MgSO4, then filtered and concentrated. The residue is purified by column chromatography on silica gel (n-hexane/AcOEt= 1/1) to obtain 3,5-dimethyl-4-hydroxy-6-(6-methoxybenzophenone-2 - yl)-2H-Piran-2-it.

Yield: 20 mg (century 1,3%)

1H NMR ( ppm, Dl3): 2,12 (s, 3H), and 2.27 (s, 3H), of 4.00 (s, 3H), from 5.50 to 6.50 (broad s, 1H), 6,80 to 7.80 (m, 4H)

Example 27. Synthesis of 3,5-dimethyl-4-hydroxy-6-(5-(5-pyrimidinylidene)benzofuran-2-yl)-2H-Piran-2-he

The solution tributylphosphine 2 N THF (0,94 ml) and the solution TMAD (323 mg) in CH2-it (118 mg) and 5-hydroxyethylpyrrolidine (202 mg) in THF (30 ml) at 0oC, the mixture is stirred at room temperature overnight. The reaction solution is cooled with ice and add 1 N aqueous solution of lithium hydroxide (5 ml), the mixture is stirred at room temperature for one hour, after which the solution is again cooled with ice, add 1 N aqueous solution of hydrochloric acid (5 ml) and AcOEt, the organic and aqueous layers separated, the aqueous layer was additionally extracted with AcOEt. The organic layers are combined and dried over MgSO4, then filtered and concentrated. The residue is purified by column chromatography on silica gel (AcOEt/MeOH=10/1) to obtain 3,5-dimethyl-4-hydroxy-6-(5-(5-

pyrimidinylidene)benzofuran-2-yl)-2H-Piran-2-it.

Yield: 35 mg (B. 26%)

1H NMR ( ppm, DMSO-d6): 1,95 (s, 3H), to 2.29 (s, 3H), of 5.24 (s, 2H), 7,12 to 7.14( m, 1H), 7,33 to 7.38 (m, 2H), up to 7.61 7,63 (m, 1H), 8,95 (s, 2H), 9,18 (s, 1H), 10,91 (broad s, 1H)

The following examples are carried out in accordance with methods similar to those described in the previous examples, using chemical methods well known to specialists in this field.

Example 28. 6-(benzofuran-2-yl)-3,5-dimethyl-4-(4-hydroxymethylbutyrate)-2H-Piran-2-he

1H NMR ( ppm, Dl3): 2,04 (s, 3H), of 2.34 (s, 3H), a 4.86 (s, 2H), 7.24 to to 7.42 (m, Naxi-N-methylamino)atomic charges)-3,5-dimethyl-2H-Piran-2-he

1H NMR ( ppm, Dl3): 1,84, a 2.00 (s, 3H), 2,14, 2,32 (s, 3H), 3,13, 3,14 (s, 3H), 4,33, 4,36 (c, 2H), 5,18, 5,20 (s, 2H); from 7.25 to the 7.43 (m, 8H), 7,53 (d, J=8.6 Hz, 1H), 7,66 (d, J=6,9 Hz, 1H)

Example 30. 6-(benzofuran-2-yl)-3,5-dimethyl-4-(4-methoxybenzyloxy-2H-Piran-2-he

1H NMR ( ppm, Dl3): 2,03 (s, 3H), of 2.34 (s, 3H), 3,93 (s, 3H),? 7.04 baby mortality (d, J=8,9 Hz, 2H), 7.24 to to 7.42 (m, 3H), 7,52 (d, J=8,2 Hz, 1H), 7,66 (d, J=7.9 Hz, 1H), 8,17 (d, J=9,2 Hz, 1H)

Example 31. 6-(benzofuran-2-yl)-3,5-dimethyl-4-phenylacetylene-2H-Piran-2-he

1H NMR ( ppm, Dl3): to 1.86 (s, 3H), and 2.14 (s, 3H), 3,93 (s, 2H), 7,21 to 7.45 (m, 8H), 7,50 (d, J=7.9 Hz, 1H), 7,63 (d, J=7.9 Hz, 1H)

Example 32. 6-(benzofuran-2-yl)-4-hydroxy-3-methyl-2H-Piran-2-he

1H NMR ( ppm, DMSO-d6): 1,85 (s, 3H), 6.73 x (s, 1H), 7.29 trend to 7.46 (m, 3H), to 7.67 (d, J=7.9 Hz, 1H), 7,73 (d, J=7,3 Hz, 1H), 11,58 (broad s, 1H)

Example 33. 6-(benzofuran-2-yl)-5-ethyl-4-hydroxy-3-methyl-2H-Piran-2-he

1H NMR ( ppm, DMSO-d6): of 1.18 (t, J=7,3 Hz, 3H), 1.93 and (s, 3H), 2,79 (sq J= 7,3 Hz, 2H), 7.29 trend to 7,44 (m, 3H), to 7.67 (d, J=8,3 Hz, 1H), 7,74 (d, J= 8,3 Hz, 1H), 10,89 (broad s, 1H)

Example 34. 6-(benzofuran-2-yl)-4-hydroxy-5-isopropyl-3-methyl-2H-Piran-2-he

1H NMR ( ppm, DMSO-d6): 1,33 (d, J=6.9 Hz, 6H), 1.93 and (s, 3H), 3.40 in to 3.56 (m, 1H), 7.29 trend to 7.46 (m, 3H), to 7.67 (d, J=8.6 Hz, 1H), 7,74 (d, J=7,6 Hz, 1H), 10,85 (s, 1H)

Example 35. 6-(benzofuran-2-yl)-4-hydroxy-3-methyl-5-phenyl-2H-Piran-2-he

1H NMR ( ppm, DMSO-is l-2H-Piran-2-on

1H NMR ( ppm, DMSO-d6): of 1.93 (s, 3H), 4,23 (s, 2H), 7,13 to 7.37 (m, 8H), a 7.62 (d, J=8,3 Hz, 1H), 7,71 (d, J=7,6 Hz, 1H), br11.01 (broad s, 1H)

Example 37. 6-(benzofuran-2-yl)-4-hydroxy-5-methoxy-3-methyl-2H-Piran-2-he

1H NMR ( ppm, DMSO-d6): 1,92 (s, 3H), 3,82 (s, 3H), 7,32 to 7.51 (m, 3H), 7,72 (doctor J=7.9 Hz, 1H), 7,78 (d, J=7,3 Hz, 1H), 11,40 (broad s, 1H)

Example 38. 6-(benzofuran-2-yl)-4-hydroxy-3-isopropyl-5-methyl-2H-Piran-2-he

1H NMR ( ppm, DMSO-d6): 1,22 (d, J=6.9 Hz, 6H), to 2.29 (s, 3H), 3,20 3,30 to (m, 1H), 7,30 to 7.45 (m, 3H), 7,68 (d, J=7.9 Hz, 1H), 7,74 (d, J=7,6 Hz, 1H), is 10.68 (s, 1H)

Example 39. 6-(benzofuran-2-yl)-3,5-dimethyl-4-isobutyryloxy-2H-Piran-2-he

1H NMR ( ppm, Dl3): of 1.39 (d, J=6.9 Hz, 6H), to 1.98 (s, 3H), to 2.29 (s, 3H), 2.83 to a 3.01 (m, 1H), 7,25 to 7.42 (m, 2H), was 7.36 (s, 1H), 7,52 (d, J=8,3 Hz, 1H), 7,65 (d, J=7,6 Hz, 1H)

Example 40. 4-acetoxy-3,5-dimethyl-6-(5-nitrobenzophenone-2-yl)-2H-Piran-2-he

1H NMR ( ppm, Dl3): 2,02 (s, 3H), 2,32 (s, 3H), 2,42 (s, 3H), 7,46 (s, 1H), to 7.64 (d, J=8,9 Hz, 1H), 8.30 to (DD. J=2,3 Hz and 8.9 Hz, 1H), 8,59 (d, J=2.3 Hz, 1H)

Example 41. 3,5-dimethyl-4-methoxyethoxy-6-(5-nitrobenzophenone-2-yl)-2H-Piran-2-he;

1H NMR ( ppm, Dl3): and 2.14 (s, 3H), 2,43 (s, 3H), of 3.64 (s, 3H), 5,14 (s, 2H), 7,43 (s, 1H), 7,63 (d, J=9.0 Hz, 1H), 8.30 to (DD,J=2.1 Hz, 9.0 Hz, 1H), 8,58 (d, J=2.1 Hz, 1H)

Example 42. 6-(benzofuran-2-yl)-3,5-dimethyl-4-phenoxyacetate-2H-Piran-2-he

1H NMR ( ppm, Dl
1H NMR ( ppm, Dl3): of 2.23 (s, 3H), of 2.50 (s, 3H), 7,28 to 7.46 (m, 3H), 7,55 (d, J=8,2 Hz, 1H), 7,68 (d, J=7,6 Hz, 1H)

Example 44. 6-(benzofuran-2-yl)-3,5-dimethyl-4-p-toluensulfonate-2H-Piran-2-he

1H NMR ( ppm, Dl3): is 1.81 (s, 3H), of 2.33 (s, 3H), of 2.51 (s, 3H), 7,28 up of 7.48 (m, 5H), 7,53 (d, J=8,2 Hz, 1H), 7,66 (d, J=7,6 Hz, 1H), of 7.90 (d, J= 8,3 Hz, 2H)

Example 45. 3,5-dimethyl-4-hydroxy-6-(5-nitrobenzophenone-2-yl)-2H-Piran-2-he

1H NMR ( ppm, CD3OD): a 1.96 (s, 3H), 2,32 (s, 3H), to 7.61 (s, 1H), 7,95 (d, J=9,2 Hz, 1H), 8.30 to (DD, J=2.3 Hz, and 9.2 Hz, 1H), 8,71 (d, J=2.3 Hz, 1H), 11,00 (broad s, 1H)

Example 46. 3,5-dimethyl-6-(5-(ethylamino)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he

1H NMR ( ppm, CD3OD): to 1.42 (t, J=7,3 Hz, 3H), 2,04 (s, 3H), 2,43 (s, 3H), 3,44 (kV, J=7,3 Hz, 2H), 7,37 (s, 1H), 7,50 (DD, J=2.0 Hz, a 8.9 Hz, 1H), 7,68 (d, J=8,9 Hz, 1H), 7,79 (d, J=2.0 Hz, 1H)

Example 47. 3,5-dimethyl-4-hydroxy-6-(5-(p-toluensulfonyl)benzofuran-2-yl)-2H-Piran-2-he

1H NMR ( ppm, CD3OD): 2,00 (s, 3H), of 2.36 (s, 6N), 7,07 to 7.11 (m, 1H), 7,21 to 7.26 (m, 2H), 7,34 to 7.41 (m, 2H), from EUR 7.57 up to 7.61 (m, 2H), 7,70 up to 7.77 (m, 1H)

Example 48. 3,5-dimethyl-6-(5-(dimethylamino)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he

1H NMR ( ppm, CD3OD): 1,95 (s, 3H), of 2.30 (s, 3H), 3,12 (C, 6N), from 7,41 to 7.75 (m, 4H)

Example 49. 6-(5-(diban), the 4.65 (s, 4H), 6.89 in to 6.94 (m, 2H), 7,07 (s, 1H), 7,13 to 7,88 (m, 11N)

Example 50. 6-(benzofuran-2-yl)-3,5-dimethyl-4-isonicotinoyl-2H-Piran-2-he

1H NMR ( ppm, Dl3): 2,04 (s, 3H), of 2.34 (s, 3H), 7,26 to 7.42 (m, 3H), 7,53 (d, J=7.9 Hz, 1H), to 7.67 (d, J=7,3 Hz, 1H), 8.03, 8,95 (Avcv, J=6.3 Hz, 4H)

Example 51. 4-(2-aminoethoxy)-6-(benzofuran-2-yl)-3,5-dimethyl-2H-Piran-2-he hydrochloride

1H NMR ( ppm, DMSO-d6): 1,96 (s, 3H), and 2.27 (s, 3H), to 4.41 (s, 2H), 7,31 to 7.50 (m, 2H), 7,55 (s, 1H), 7,71 (d, J=8,3 Hz, 1H), 7,78 (d, J=7.9 Hz, 1H), 8,61 (broad s, 3H)

Example 52. 6-(5-benzyloxybenzophenone-2-yl)-4(2-(tert-butoxycarbonylamino)atomic charges)-3,5-dimethyl-2H-Piran-2-he

1H NMR ( ppm, Dl3): to 1.48 (s, N), from 2.00 (s, 3H), of 2.30 (s, 3H),4,23 (d, J= 5,9 Hz, 2H), from 5,06 up to 5.14 (m, 1H), 5,11 (s, 2H), 7,06 (DD, J=2,6 Hz and 8.9 Hz, 1H), 7,14 (d, J=2.6 Hz, 1H), 7,27 to 7.50 (m, 7H)

Example 53. 4-(2-aminoethoxy)-6-(5-benzyloxybenzophenone-2-yl)-3,5-di-methyl-2H-Piran-2-he hydrochloride

1H NMR ( ppm, DMSO-d6): 1,95 (3H), 2,24 (3N), to 4.41 (2H), 5,16 (2N), 7,13 (d, J=9,2 Hz, 1H), 7.29 trend to 7.51 (m, 7H), a 7.62 (d, J=9.6 Hz, 1H), to 8.57 (broad s, 2H)

Example 54. 4-(4-(acetylamino)benzoyloxy)-6-(5-benzyloxybenzophenone-2-yl)-3,5-dimethyl-2H-Piran-2-he

1H NMR ( ppm, Dl3): 2,02 (s, 3H), and 2.26 (s, 3H), 2,31 (s, 3H), 5,12 (s, 2H), 7,06 (DD, J=2,6 Hz and 8.9 Hz, 1H), 7,15 (d, J=2.6 Hz, 1H), 7,21 to 7.50 (m, 8H), 7,72 (d, J=8,9 Hz, 1H), 8,18 (d, J=8,9 Hz is m, Dl3): 2,04 (s, 3H), of 2.33 (s, 3H), 5,12 (s, 2H), 7,07 (DD, J=2,6 Hz and 8.9 Hz, 1H), 7,16 (d, J=2.6 Hz, 1H), 7,31 to 7.60 (m, 8H), 8,48 (d, J=7.9 Hz, 1H), 8,94 (broad s, 1H), 9,43 (s, 1H)

Example 56. 6-(5-benzyloxybenzophenone-2-yl)-3,5-dimethyl-4-isonicotinoyl-2H-Piran-2-he

1H NMR ( ppm, Dl3): 2,03 (s, 3H), 2,32 (s, 3H), 5,12 (s, 2H), 7,07 (DD, J=2.3 Hz, a 8.9 Hz, 1H), 7.16 (d, J=2.3 Hz, 1H), 7,30 to 7.50 (m, 7H), 8,03 (d, J=5,9 Hz, 2H), to 8.94 (d, J=5,9 Hz, 2H)

Example 57. 6-(5-benzyloxybenzophenone-2-yl)-5-ethyl-4-hydroxy-3-methyl-2H-Piran-2-he

1H NMR ( ppm, DMSO-d6): 1,17 (t, J=7,3 Hz, 3H), 1.93 and (s, 3H), 2,78 (kV, J= 7,3 Hz, 2H), 5,14 (s, 2H), 7,07 (DD, J=2,6 Hz and 8.9 Hz, 1H), 7,29 up of 7.48 (m, 7H), EUR 7.57 (d, J=9,2 Hz, 1H), 10,87 (broad s, 1H)

Example 58. 5-ethyl-4-hydroxy-3-methyl-6-(5-(3 - pyrimidinylidene)benzofuran-2-yl)-2H-Piran-2-he

1H NMR ( ppm, DMSO-d6): 1,24 (t, J=7,3 Hz, 3H), of 1.99 (s, 3H), 2,93 (kV, J= 7,3 Hz, 2H), 5,20 (s, 2H), 7,07 to 7.10 (m, 1H), 7,27 to 7,28 (m, 2H), 7,45 to 7.49 (m, 2H), of 7.97 (d, J=7,6 Hz, 1H), 8,51 (m, 1H), 8,67 (s, 1H)

Example 59. 4 atomic charges-3,5-dimethyl-6-(5-(2-thiazoleacetate)benzofuran-2-yl)-2H-Piran-2-he

1H NMR ( ppm, Dl3): to 2.13 (s, 3H), of 2.34 (s, 3H), 2,41 (s, 3H), and 5.30 (s, 2H), to 7.09 (DD, J=8.6 Hz, 2.4 Hz, 1H), 7,32 (c, 1H), was 7.36 (d, J=1.9 Hz, 1H), 7,47 (d, J=1.9 Hz, 1H), 7,51 (d, J=8.6 Hz, 1H), 7,86 (d, J=2.4 Hz, 1H)< / BR>
Example 60. 4-hydroxy-3,5-dimethyl-6-(5-(2-thiazoleacetate)benzofuran-2-yl)-2H-Piran-2-he

1H NMR ( RR is, J=3.2 Hz, 1H), 9,40 (s, 1H)

Example 61. 6-(benzofuran-2-yl)-3,5-dimethyl-4-(3-phenylpropionylamino)-2H-Piran-2-he

1H NMR ( ppm, Dl3): to 1.86 (s, 3H), of 2.16 (s, 3H), 2.94 to 3.18(m, 4H), 7.20 to 7.41(m, 8H), 7,52 (d, J=7.9 Hz, 1H), to 7.64 (d, J=7,6 Hz, 1H)

Example 62. 6-(benzofuran-2-yl)-3,5-dimethyl-4-(2-pyrolox)-2H-Piran-2-he

1H NMR ( ppm, Dl3): 2,04 (s, 3H), of 2.35 (s, 3H), to 6.67 (DD, J=1.7 Hz, 3.6 Hz, 1H), 7,25 to 7.42 (m, 2H), 7,38 (s, 1H), 7,50 (d, J=3.6 Hz, 1H), 7,53 (d, J=8.6 Hz, 1H), 7,66 (d, J=7,6 Hz, 1H), 7,76 (d, J=1.7 Hz, 1H)

Example 63. 6-(benzofuran-2-yl)-3,5-dimethyl-4-nicotinergic-2H-Piran-2-he

1H NMR ( ppm, Dl3): 2,05 (s, 3H), of 2.36 (s, 3H), 7,26 to the 7.43 (m, 3H), from 7.50 to 7.60 (m, 2H), to 7.67 (d, J=7,6 Hz, 1H), 8,49 (d, J=7.9 Hz, 1H), 8,95 (d, J=4.3 Hz, 1H), 9,44 (s, 1H)

Example 64. 6-(benzofuran-2-yl)-3,5-dimethyl-4-(2-acetylamino-4-(morpholine-4-yl)-4-oxobutyrate)-2H-Piran-2-he

1H NMR ( ppm, Dl3): a 2.01 (s, 3H), of 2.05 (s, 3H), of 2.33 (s, 3H), of 3.00 (DD, J= 4.4 Hz, is 16.8 Hz, 1H), and 3.16 (DD, J=7,6 Hz, is 16.8 Hz, 1H), 3,60 up to 3.73 (m, 8H), lower than the 5.37 to 5,44 (m, 1H), 6,44 (d, J=9,3 Hz, 1H), 7,27 to 7.40 (m, 3H), 7,52 (d, J=8,3 Hz, 1H), 7,65 (d, J=7,3 Hz, 1H)

Example 65. 4 atomic charges-6-(5-bromobenzophenone-2-yl)-3,5-dimethyl-2H-Piran-2-he

1H NMR ( ppm, Dl3): 2,00 (s, 3H), of 2.30 (s, 3H), 2.40 a (s, 3H), 7,29 (s, 1H), 7,40 (d, J=8,9 Hz, 1H), 7,47 (DD, J=8,9 Hz, 2.2 Hz, 1H), 7,78 (d, J=2.2 Hz, 1H)

Example 66. 6-(benzofuran-2-yl)-5-cyclopentyl is to 2.17 (m, 1H), 2,90 (d, J=7,3 Hz, 2H), 7.29 trend to 7,44 (m, 3H), of 7.65 (d, J=8,2 Hz, 1H), 7,74 (d, J=7,3 Hz, 1H), 10,85 (s, 1H)

Example 67. 6-(benzofuran-2-yl)-4-hydroxy-3-methyl-5-phenoxy-2H-Piran-2-he

1H NMR ( ppm, DMSO-d6): 2,03 (s, 3H), 7,11 up 7,22 (m, 3H), 7,32 to 7.49 (m, 5H), of 7.69 (d, J=8,3 Hz, 1H), 7,76 (d, J=7,6 Hz, 1H), to 11.56 (broad s, 1H)

Example 68. 6-(benzofuran-2-yl)-5-(2-butenyl)-4-hydroxy-3 - methyl-2H-Piran-2-he

1H NMR ( ppm, DMSO-d6): from 1,70 to 1.78 (m, 3H), 2,03 (s, 3H), 3,57 to 3.64 (m, 2H), 5,61 to 5,67 (m, 2H), 7,39 to 7.54(m, 3H), 7,78 (d, J=8,3 Hz, 1H), to 7.84 (d, J=7,6 Hz, 1H), 11,00 (broad s, 1H)

Example 69. 6-(benzofuran-2-yl)-4-(1-carbobenzoxy-2-pyrrolidone-5-icebox)-3,5-dimethyl-2H-Piran-2-he

1H NMR ( ppm, Dl3): of 1.94 (s, 3H), of 2.25 (s, 3H), 2.30 to 2.40 (m, 1H), from of 2.51 to 2.88 (m, 3H), of 5.03 (DD, J=2,6 Hz and 8.9 Hz, 1H), 5,33, 5,38 (Avcv, J=2.2 Hz, 2H), 7,28 up of 7.48 (m, 8H), 7,52 (d, J=8.6 Hz, 1H), 7,66 (d, J=7.9 Hz, 1H)< / BR>
Example 70. 6-(benzofuran-2-yl)-3,5-dimethyl-4-(2-pyrrolidone-5-icebox)-2H-Piran-2-he

1H NMR ( ppm, DMSO-d6): 1,91 (s, 3H), of 2.23 (s, 3H), 2,19 to 2.38 (m, 3H), 2,47 to 2.66 (m, 1H), 4,65 up to 4.73 (m, 1H), 7,31 to 7.40 (m, 1H), 7,41 to 7.50 (m, 1H), 7,53 (s, 1H), 7,71 (d, J=8,3 Hz, 1H), to 7.77 (d, J=7,6 Hz, 1H), 8.34 per (s, 1H)

Example 71. 6-(benzofuran-2-yl)-4-(2-tert-butoxycarbonylamino)atomic charges)-3,5-dimethyl-2H-Piran-2-he

1H NMR ( ppm, Dl3): to 1.48 (s, N), from 2.00 (s, 3H), 2,32 (s, 3H), 4,23 (d, J= 6.3 Hz, 2H), 5,10 (chillaxe)-3,5-dimethyl-2H-Piran-2-he

1H NMR ( ppm, Dl3): 2,05 (s, 3H), of 2.35 (s, 3H), 3,92 (s, 3H), of 3.95 (s, 3H), from 6,54 to 6.66 (m, 2H), 7,25 to 7.41 (m, 3H), 7.52 (d, J=8,2 Hz, 1H), 7,65 (d, J=7,6 Hz, 1H), 8,08 (d, J=8.6 Hz, 1H)

Example 73. 6-(benzofuran-2-yl)-4-(2,6-dimethoxybenzoate)- 3,5-dimethyl-2H-Piran-2-he

1H NMR ( ppm, Dl3): 2,17 (s, 3H), 2,48 (s, 3H), 3,91 (C, 6N), of 6.65 (d, J=8,3 Hz, 2H), from of 7.25 to 7.45 (m, 4H), 7,54 (d, J=8,2 Hz, 1H), 7,66 (d, J=7.9 Hz, 1H)

Example 74. 6-(benzofuran-2-yl)-3,5-dimethyl-4-(6-hydroxynicotinate)-2H-Piran-2-he

1H NMR ( ppm, DMSO-d6): 1,91 (s, 3H), 2,24 (s, 3H), 6.48 in (d, J=9.9 Hz, 1H), 7,31 to 7.50 (m, 2H), 7,54 (s, 1H), 7,71 (d, J=8,3 Hz, 1H), 7,78 (d, J=7.9 Hz, 1H), 7,95 (d, J=9.9 Hz, 1H), 8,43 (s, 1H), 12,51 (broad s, 1H)

Example 75. 6-(benzofuran-2-yl) -3, 5-dimethyl-4(3-dimethylaminobenzoate)-2H-Piran-2-he

1H NMR ( ppm, DMSO-d6): 2,04 (s, 3H), of 2.35 (s, 3H), 3,05 (C, 6N),? 7.04 baby mortality (DD, J= 2,6 Hz, 8.6 Hz, 1H); from 7.25 to 7,44 (m, 4H), of 7.48 to 7.59 (m, 3H), 7,66 (d, J=7,6 Hz, 1H)

Example 76. 4-(4-(acetylamino)benzoyloxy)-6-(benzofuran-2-yl)-3,5-dimethyl-2H-Piran-2-he

1H NMR ( ppm, Dl3): 2,03 (s, 3H), and 2.26 (s, 3H), of 2.33 (s, 3H), 7,24 to 7.41 (m, 3H), 7,49 (s, 1H), 7,52 (d, J=8,2 Hz, 1H), 7,66 (d, J=7,6 Hz, 1H), 7,73 (d, J=8.6 Hz, 2H), 8,18 (d, J=8.6 Hz, 2H)

Example 77. 3,5-dimethyl-6-(6-(2-forbindelse)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 381,

Example 78. 3,5-dimethyl-6-(5-(2-forbindelse)b is benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 397,0

Example 80. 6-(6-(2-bromobenzylamine)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis; [M++ N] = 442,0

Example 81. 6-(5-(2-bromobenzylamine)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 442,0

Example 82. 6-(6-(3-bromobenzylamine)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 442,0

Example 83. 6-(5-(3-bromobenzylamine)benzofuran-2-yl^-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 442,0

Example 84. 3,5-dimethyl-4-hydroxy-6-(6-(3,4-(methylendioxy)benzyloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 407,0

Example 85. 3,5-dimethyl-4-hydroxy-6-(5-(3,4-(methylendioxy) benzyloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 407,0

Example 86. 3,5-dimethyl-4-hydroxy-6-(6-(2-pyridyloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 364,0

Example 87. 3,5-dimethyl-4-hydroxy-6-(5-(2-pyridyloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 364,0

Example 88. 3,5-dimethyl-4-hydroxy-6-(6-(3-pyridyloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 364,0

Example 89. 3,5-dimethyl-4-hydroxy-6-(5-(3-pyridyloxy)benzop the XI)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 364,0

Example 91. 3,5-dimethyl-4-hydroxy-6-(5-(4-pyridyloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 364,0

Example 92. 3,5-dimethyl-4-hydroxy-6-(6-tetrahydrofuran-3-ylethoxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 357,0

Example 93. 3,5-dimethyl-4-hydroxy-6-(5-(-tetrahydrofuran-3-ylethoxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 357,0

Example 94. 3,5-dimethyl-4-hydroxy-6-(6-(1-methylpiperidin-2-ylethoxy)beaufurn-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 384,0

Example 95. 3,5-dimethyl-4-hydroxy-6-(5-(1-methylpiperidin-2-ylethoxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 384,0

Example 96. 3,5-dimethyl-4-hydroxy-6-(6-(1-methylpiperidin-3-ylethoxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 384,0

Example 97. 3,5-dimethyl-4-hydroxy-6-(5-(1-methylpiperidin-3-ylethoxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 384,0

Example 98. 3,5-dimethyl-4-hydroxy-6-(6-(1-methyl-3-piperidinyloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 370,0

Example 99. 3,5-dimethyl-4-hydroxy-6-(5-(1-methyl-3-piperidinyloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 370,0

+ + N] = 356,0

Example 101. 3,5-dimethyl-4-hydroxy-6-(5-(1-methyl-3-pyrrolidinyloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 356,0

Example 102. 3,5-dimethyl-4-hydroxy-6-(6-(2-pyrrolidinyloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 370,0

Example 103. 3,5-dimethyl-4-hydroxy-6-(5-(2-pyrrolidinyloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 370,0

Example 104. 6-(6-(4-(diethylamino)-1-methylbutoxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis; [M++ N] = 414,0

Example 105. 6-(5-(4-(diethylamino-1 methylbutoxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 414,0

Example 106. 6-(6-(1,3-bis(dimethylamino)-2-propoxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 401,0

Example 107. 6-(5-(1,3-bis(dimethylamino)-2-propoxy)benzofuran-2-yl) -3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 401,0

Example 108. 3,5-dimethyl-4-hydroxy-6-(6-(2-pyrrolidone-5-ylethoxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 370,0

Example 109. 3,5-dimethyl-4-hydroxy-6-(5-(2-pyrrolidone-5-ylethoxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 370,0

Example 110. 6-(6-chromium is 6-(5-(chroman-4-roxypanther-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 405,0

Example 112. 6-(6-(1-n-butoxycarbonyl)ethoxy)-benzofuran-2-yl)--3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 401,0

Example 113. 6-(5-(1-(n-butoxycarbonyl)ethoxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 401,0

Example 114. 3,5-dimethyl-4-hydroxy-6-(6-(2-morpholine-4-yl)ethoxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 386,0

Example 115. 3,5-dimethyl-4-hydroxy-6-(5-(2-(morpholine-4-yl)ethoxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 386,0

Example 116. 6-(6-(4-carboxyphenoxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 407,0

Example 117. 6-(5-(4-carboxyphenoxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 407,0

Example 118. 6-(6-(4-chlorobenzoyloxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 397,0

Example 119. 3, 5-dimethyl-4-hydroxy-6-(6-(2-(trifluoromethyl) benzyloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 431,0

Example 120. 3,5-dimethyl-4-hydroxy-6-(5-(2-(trifluoromethyl) benzyloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 431,0

Example 121. 3,5-di is

Example 122. 3,5-dimethyl-4-hydroxy-6-(5-(3-(trifluoromethyl) benzyloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 431,0

Example 123. 3,5-dimethyl-4-hydroxy-6-(6-(4-(trifluoromethyl) benzyloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 431,0

Example 124. 3,5-dimethyl-4-hydroxy-6-(5-(4-trifluoromethyl) benzyloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 431,0

Example 125. 6-(6-(cyclopentyloxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 355,0

Example 126. 6-(5-(cyclopentyloxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 355,0

Example 127. 6-(6-(cyclopropylmethoxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2 N-Piran-2 he

Mass analysis: [M++ N] = 327,0

Example 128. 6-(5-(cyclopropylmethoxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 327,0

Example 129. 6-(6-(2,4-dimethylbenzylamine)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 391,0

Example 130. 6-(5-(2,4-dimethylbenzylamine)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 391,0

Example 131. 6-(6-(2,5-dimethylbenzylamine)benzofuran-2-yl)-3,5-Demetron-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 391,0

Example 133. 6-(6-(3,4-dimethylbenzylamine)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 391,0

Example 134. 6-(5-(3,4-dimethylbenzylamine)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 391,0

Example 135. 6-(6-(3,5-dimethylbenzylamine)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 391,0

Example 136. 6-(5-(3,5-dimethylbenzylamine)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 391,0

Example 137. 3,5-dimethyl-4-hydroxy-6-(6-((2-thienyl)methoxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 369,0

Example 138. 3,5-dimethyl-4-hydroxy-6-(5-((2-thienyl)methoxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 369,0

Example 139. 3,5-dimethyl-6-(6-((2-furyl)methoxy)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 353,0

Example 140. 3,5-dimethyl-6-(5-((2-furyl)methoxy)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 353,0

Example 141. 3,5-dimethyl-4-hydroxy-6-(6-(2-phenoxyethoxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 392,0

Example 142. 3,5-dimethyl-4-hydroxy-6-(5-(2-phenoxyethoxy)benzofuran-phenyl)ethoxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 445,0

Example 144. 3,5-dimethyl-4-hydroxy-6-(5-(1-(2-(trifluoromethyl)phenyl)ethoxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 445,0

Example 145. 6-(6-(2-chloro-5-nitrobenzyloxy)benzofuran-2-yl-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 442,0

Example 146. 6-(6-(3-chloro-6-nitrobenzyloxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 442,0

Example 147. 6-(5-(3-chloro-6-nitrobenzyloxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 442,0

Example 148. 6-(6-(2-cyclohexylmethoxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = OF 383.0

Example 149. 6-(5-(2-cyclohexylmethoxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = OF 383.0

Example 150. 3,5-dimethyl-4-hydroxy-6-(6-(1,4-pentadien-3-yloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 339,0

Example 151. 3,5-dimethyl-4-hydroxy-6-(5-(1,4-pentadien-3-yloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 339,0

Example 152. 6-(6-(2,4-dichloraniline)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 432,0

Example 153. 6-(5-(2,4-deharbe 6-(6-(2,5-dichloraniline)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 432,0

Example 155. 6-(5-(2,5-dichloraniline)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 432,0

Example 156. 6-(6-(2, 6-DICHLOROSILANE)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 432,0

Example 157. 6-(5-(2,6-DICHLOROSILANE)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 432,0

Example 158. 6-(6-(3,4-dichloraniline)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 432,0

Example 159. 6-(5-(3,4-dichloraniline)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 432,0

Example 160. 6-(6-(3,5-dichloraniline)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 432,0

Example 161. 6-(5-(3,5-dichloraniline)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 432,0

Example 162. 6-(6-(4-n-butoxybenzoate)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 435,0

Example 163. 6-(5-(4-n-butoxybenzoate)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 435,0

Example 164. 3,5-dimethyl-4-hydroxy-6-(-6-(3-methyl-2 is hydroxy-6-(5-(3-methyl-2-nitrobenzyloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 422,0

Example 166. 3,5-dimethyl-6-(6-(2,3-dimethyl-4-methoxybenzyloxy) benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 421,0

Example 167. 3,5-dimethyl-6-(5-(2,3-dimethyl-4-methoxybenzyloxy) benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 421,0

Example 168. 3,5-dimethyl-6-(6-(3,5-dinitrobenzoate)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 453,0

Example 169. 3,5-dimethyl-6-(5-(3,5-dinitrobenzoate)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 453,0

Example 170. 3,5-dimethyl-4-hydroxy-6-(6-(1,2,3,4-tetrahydronaphthalen-1 yloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 403,0

Example 171. 3,5-dimethyl-4-hydroxy-6-(5-(1,2,3,4-tetrahydronaphthalen-1 yloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 403,0

Example 172. 3,5-dimethyl-4-hydroxy-6-(6-(1-aftermatket)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 413,0

Example 173. 3,5-dimethyl-4-hydroxy-6-(5-(1-aftermatket)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 413,0

Example 174. 3,5-dimethyl-4-hydroxy-6-(6-(2-aftermatket)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 413,0

Example 175. Example 176. 6-(6-(1,4-benzodioxan-2-ylethoxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 421,0

Example 177. 6-(5-(1,4-benzodioxan-2-ylethoxy)benzofuran-2-yl)-3,5-dimethyl)-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 421,0

Example 178. 3,5-dimethyl-6-(6-(3-HEXEN-1-yloxy)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 355,0

Example 179. 3,5-dimethyl-6-(5-(3-HEXEN-1-yloxy)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 355,0

Example 180. 6-(6-(2-butyn-1 yloxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 325,0

Example 181. 6-(5-(2-butyn-1 yloxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 325,0

Example 182. 3,5-dimethyl-6-(6-(2,2-dimethyl-1,3-dioxolane-4-ylethoxy)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 387,0

Example 183. 3,5-dimethyl-6-(5-(2,2-dimethyl-1,3-dioxolane-4-ylethoxy)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 387,0

Example 184. 3,5-dimethyl-6-(6-(2-ethoxyethoxy)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 345,0

Example 185. 3,5-dimethyl-6-(5-(2-ethoxyethoxy)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-Ouran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 357,0

Example 187. 3,5-dimethyl-4-hydroxy-6-(5-(3-methyloxiran-3-ylethoxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 357,0

Example 188. 3,5-dimethyl-6-(6-(5-hexyne-1-yloxy)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 353,0

Example 189. 3,5-dimethyl-6-(5-(5-hexyne-1-yloxy)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 353,0

Example 190. 3,5-dimethyl-6-(6-(5-HEXEN-1-yloxy)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 355,0

Example 191. 3,5-dimethyl-6-(5-(5-HEXEN-1-yloxy)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 355,0

Example 192. 3,5-dimethyl-6-(6-(2,2-DIMETHYLPROPANE(benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 343,0

Example 193. 3,5-dimethyl-6-(5-(2,2-DIMETHYLPROPANE)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 343,0

Example 194. 3,5-dimethyl-6-(6-{ 2,2-diphenylmethoxy)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 453,0

Example 195. 3,5-dimethyl-6-(5-(2,2-diphenylmethoxy)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 453,0

Example 196. 3,5-dimethyl-4-hydroxy-6-(6-(2-phenyl-2-propoxy)benzofuran-benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 391,0

Example 198. 3,5-dimethyl-4-hydroxy-6-(6-(2-(1-naphthyl)ethoxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 427,0

Example 199. 3,5-dimethyl-4-hydroxy-6-(5-(2-(1-naphthyl)ethoxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 427,0

Example 200. 6-(6-(bis(4-methoxyphenyl)methoxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 499,0

Example 201. 6-(5-(bis(4-methoxyphenyl)methoxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 499,0

Example 202. 3,5-dimethyl-4-hydroxy-6-(6-(3-phenylpropoxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 391,0

Example 203. 3,5-dimethyl-4-hydroxy-6-(5-(3-phenylpropoxy)

benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 391,0

Example 204. 3,5-dimethyl-4-hydroxy-6-(6-(4-phenylmethoxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 405,0

Example 205. 3,5-dimethyl-4-hydroxy-6-(5-(4-phenylmethoxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 405,0

Example 206. 6-(6-(cyclohexylmethoxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 369,0

Example 207. 6-(5-(cyclohexylmethoxy)benzofuran-2-yl)-3,5-dsaparam-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 397,0

Example 209. 6-(5-(3-cyclohexylpropionic)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 397,0

Example 210. 6-(6-(3-butene-1 yloxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 327,0

Example 211. 6-(5-(3-butene-1 yloxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 327,0

Example 212. 6-(6-(2-(benzyloxy)ethoxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 407,0

Example 213. 6-(5-(2-benzyloxy)ethoxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 407,0

Example 214. 3,5-dimethyl-4-hydroxy-6-(6-(2-propyne-1-yloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 311,0

Example 215. 3,5-dimethyl-4-hydroxy-6-(5-(2-propyne-1-yloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 311,0

Example 216. 3,5-dimethyl-6-(6-(5-(etoxycarbonyl)pentyloxy)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 415,0

Example 217. 3,5-dimethyl-6-(5-(5-(etoxycarbonyl)pentyloxy)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 415,0

Example 218. 3,5-dimethyl-6-(6-ethoxybenzene-2-and dibenzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 329,0

Example 220. 6-(5-(1-tert-butoxycarbonylamino-2-ylethoxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 470,0

Example 221. 6-(5-(1-tert-butoxycarbonylamino-4-ylethoxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 470,0

Example 222. 6-(5-(1-tert-butoxycarbonylamino-4-yloxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 456,0

Example 223. 6-(5-(l-tert-butoxycarbonylamino-3-yloxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 442,0

Example 224. 6-(5-(4(tert-butoxycarbonylamino) butoxy)benzofuran-2-yl)-3, 5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 444,0

Example 225. 3,5-dimethyl-6-(6-(3-forbindelse)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 381,0

Example 226. 3,5-dimethyl-6-(5-(3-forbindelse)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 381,0

Example 227. 3,5-dimethyl-6-(6-(4-forbindelse)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 381,0

Example 228. 3,5-dimethyl-6-(5-(4-forbindelse)benzofuran-2-yl)-4-hydroxy-2H-Piran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 408,0

Example 230. 3,5-dimethyl-4-hydroxy-6-(5(2 nitrobenzyloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 408,0

Example 231. 3,5-dimethyl-4-hydroxy-6-(6-(3-nitrobenzyloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 408,0

Example 232. 3,5-dimethyl-4-hydroxy-6-(5-(3-nitrobenzyloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 408,0

Example 233. 3,5-dimethyl-4-hydroxy-6-(6-(4-nitrobenzyloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 408,0

Example 234. 3,5-dimethyl-4-hydroxy-6-(5-(4-nitrobenzyloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] =408,0

Example 235. 3,5-dimethyl-4-hydroxy-6-(6-(3-methoxybenzyloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 393,0

Example 236. 3,5-dimethyl-4-hydroxy-6-(5-(3-methoxybenzyloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 393,0

Example 237. 3,5-dimethyl-4-hydroxy-6-(6-(4-methoxybenzyloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 393,0

Example 238. 3,5-dimethyl-4-hydroc;si-6-(5-(4-methoxybenzyloxy)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 393,0

Example 239. 6-(6-(2-chlorobenzoyloxy)benzofuran-2-yl)-3,5-dimethyl-4-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 397,0

Example 241. 6-(6-(3-chlorobenzoyloxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 397,0

Example 242. 6-(5-(3-chlorobenzoyloxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 397,0

Example 243. 3,5-dimethyl-4-hydroxy-6-(5-(5-triazolylmethyl)benzofuran-2-yl)-2H-Piran-2-he

1H NMR ( ppm, DMSO-d6): of 1.93 (s, 3H), of 2.28 (s, 3H), 5,44 (s, 2H), was 7.08 (DD, J= 8,9 Hz, 2.7 Hz, 1H), 7,31 (s, 1H), 7,37 (d, J=2.7 Hz, 1H), to 7.59 (d, J=8,9 Hz, 1H), 8,02 (s, 1H), 9,11 (s, 1H)

Example 244. 4 atomic charges-6-(5-(2,4-dichloro-5-triazolylmethyl)benzofuran-2-yl)-3,5-dimethyl-2H-Piran-2-he

1H NMR ( ppm, DCl3): 2,00 (s, 3H), of 2.30 (s, 3H), 2,39 (s, 3H), to 5.21 (s, 2H), 7,01 (DD, J=a 8.9 Hz and 2.4 Hz, 1H),? 7.04 baby mortality (d, J=8,9 Hz, 1H), 7,27 (d, J=2.4 Hz, 1H), 7,44 (d, J=8,9 Hz, 1H)

Example 245. 3,5-dimethyl-4-hydroxy-6-(5-(2-(morpholinomethyl)-5-triazolylmethyl)benzofuran-2-yl)-2H-Piran-2-he

1H NMR ( ppm, DMSO-d6): 1,94 (s, 3H), to 2.29 (s, 3H), 3,15-3,18 (m, 4H), 3.64 to to 3.67 (m, 4H), of 5.53 (s, 2H), 7,12 (DD, J=8,8 Hz, 2.7 Hz, 1H), 7,34 (s, 1H), 7,39 (d, J=2.7 Hz, 1H), 7,63 (d, J=8,8 Hz, 1H), compared to 8.26 (s, 1H)

Example 246. 3,5-dimethyl-4-hydroxy-6-(5-(3-teenrotica)benzofuran-2-yl)-2H-Piran-2-he

1H NMR ( ppm, CD3D): of 1.93 (s, 3H), 2,33 (3, 3H), 5,13 (s, 2H), 7,02 (DD, J= 8,9 Hz, 2.7 Hz, 1H), 7,18 (d, J=2.7 Hz, 1H), 7,20 (s, 1H), 7,24 (d, J=2.7 Hz, 1H), 7,39 to 7.4 is n

1H NMR ( ppm, DCl3): 1,91 (s, 3H), 2,31 (s, 3H), 2.98 to 3,03 (m, 4H), 3,71 up to 3.75 (m, 4H), 5,38 (s, 2H), 7,03 (DD, J=8,9 Hz, 2.7 Hz, 1H), 7,19 (s, 1H), 7,27 to 7.29 (m, 2H), 7,51 (d, J=2.7 Hz, 1H)

Example 248. 4 atomic charges-3,5-dimethyl-6-(5-(2-(morpholinomethyl)-5-teenrotica)benzofuran-2-yl)-2H-Piran-2-he

1H NMR ( ppm, DCl3): 2,00 (s, 3H), of 2.30 (s, 3H), 2.40 a (s, 3H), 3.06 to 3,10 (m, 4H), 3,74 to 3,81 (m, 4H), from 5.29 (s, 2H),? 7.04 baby mortality (DD, J=9,2 Hz, 2.7 Hz, 1H), 7,15 (d, J=2.7 Hz, 1H), 7.31(s, 1H), 7.43 to 7.47(m, 2H)

Example 249. 3,5-dimethyl-4-hydroxy-6-(5-(4-oxazolidinone) benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 354,0

Example 250. 6-(5-(N-benzoyl-N-methylamino)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he

Mass analysis: [M++ N] = 390.0

Example 251. 3,5-dimethyl-4-hydroxy-6-(5-(N-methyl-N-(phenylacetyl)amino)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 404,5

Example 252. 3,5-dimethyl-4-hydroxy-6-(5-(N-methyl-N-(2-thienylboronic)amino)benzofuran-2-yl-2H-Piran-2-he

Mass analysis: [M++ N] = 396,0

Example 253. 3,5-dimethyl-4-hydroxy-6-(5-(N-methyl-N-(3-pyridylcarbonyl)amino)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] = 391,0

Example 254. 3, 5-dimethyl-4-hydroxy-6-(5-(N-isobutyryl-N-methylamino)benzofuran-2-yl)-2H-Piran-2-he

Mass analysis: [M++ N] =R>
Mass analysis: [M++ N] = 386,0

The following compounds are also getting similar to the methods described in the previous examples and in the examples of the preparation of the intermediate products according to the methods known to experts in this field.

Example 256. 6-(5-benzylaminopurine-2-yl)-4-benzoyloxy-3,5-dimethyl-2H-Piran-2-it.

Example 257. 4 atomic charges-3,5-dimethyl-6-(5-triftoratsetilatsetonom-2-yl)-2H-Piran-2-it.

Example 258. 6-(4-benzyloxybenzophenone-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-it.

Example 259. 4 atomic charges-3,5-dimethyl-6-(5-(methoxycarbonyl)benzofuran-2-yl)-2H-Piran-2-it.

Example 260. 4 atomic charges-6-(4-benzyloxybenzophenone-2-yl)-3,5-dimethyl-2H-Piran-2-it.

Example 261. 4 atomic charges-3,5-dimethyl-6-(5-hydroxybenzophenone-2-yl)-2H-Piran-2-it.

Example 262. 3,5-dimethyl-4-hydroxy-6-(5-hydroxybenzophenone-2-yl)-2H-Piran-2-it.

Example 263. 4 atomic charges-3,5-dimethyl-6-(5-(4-methoxybenzyloxy)benzofuran-2-yl)-2H-Piran-2-it.

Example 264. 4-(atomic charges-6-(5-carboxybenzene-2-yl)-3,5-dimethyl-2H-Piran-2-it.

Example 265. 4 atomic charges-6-(4-acetyloxybenzoic-2-yl)-3,5-dimethyl-2H-Piran-2-it.

Example 266. 4 atomic charges-3,5-dimethyl-6-(4-methoxybenzophenone-2-yl)-2H-PI. 4 atomic charges-3,5-dimethyl-6-(5-methoxybenzophenone-2-yl)-2H-Piran-2-it.

Example 269. 4 atomic charges-6-(5-acetyloxybenzoic-2-yl)-3,5-dimethyl-2H-Piran-2-it.

Example 270. 4 atomic charges-6-(5-benzyloxybenzophenone-2-yl)-3,5-dimethyl-2H-Piran-2-it.

Example 271. 6-(5-benzyloxybenzophenone-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-it.

Example 272. 3,5-dimethyl-4-hydroxy-6-(6-hydroxybenzophenone-2-yl)-2H-Piran-2-it.

Example 273. 4 atomic charges-3,5-dimethyl-6-(6-methoxybenzophenone-2-yl)-2H-Piran-2-it.

Example 274. 4 atomic charges-3,5-dimethyl-6-(5-p-toluensulfonate-2-yl)-2H-Piran-2-it.

Example 275. 4 atomic charges-6-(6-acetyloxybenzoic-2-yl)-3,5-dimethyl-2H-Piran-2-it.

Example 276. 6-(6-cyclohexylacetophenone-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-it.

Example 277. 3,5-dimethyl-4-hydroxy-6-(6-triftoratsetilatsetonom-2-yl)-2H-Piran-2-it.

Example 278. 4 atomic charges-3,5-dimethyl-6-(6-(2-(methoxycarbonyl, )ethoxy)benzofuran-2-yl)-2H-Piran-2-it.

Example 279. 3,5-dimethyl-4-hydroxy-6-(6-(2-(methoxycarbonyl)ethoxy)benzofuran-2-yl)-2H-Piran-2-it.

Example 280. 4 atomic charges-6-(6-(2-(the atomic charges)ethoxyresorufin-2-yl)-3,5-dimethyl-2H-Piran-2-it.

Example 281. 3,5-dimethyl-4-hydroc-yl)-2H-Piran-2-it.

Example 283. 3,5-dimethyl-4-hydroxy-6-(4-hydroxybenzophenone-2-yl)-2H-Piran-2-it.

Example 284. 4 atomic charges-6-(7-acetyloxybenzoic-2-yl)-3,5-dimethyl-2H-Piran-2-it.

Example 285. 4 atomic charges-6-(7-benzyloxybenzophenone-2-yl)-3,5-dimethyl-2H-Piran-2-it.

Example 286. 6-(7-benzyloxybenzophenone-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-it.

Example 287. 4 atomic charges-6-(benzofuran-2-yl)-3-isopropyl-5-methyl-2H-Piran-2-it.

Example 288. 6-(4,6-dimethoxybenzophenone-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-it.

Example 289. 4 atomic charges-6-(4,6-dimethoxybenzophenone-2-yl)-3,5-dimethyl-2H-Piran-2-it.

Example 290. 3,5-dimethyl-4-hydroxy-6-(5-(methoxycarbonyl)benzofuran-2-yl)-2H-Piran-2-it.

Example 291. 3,5-dimethyl-4-hydroxy-6-(6-methoxyethoxymethyl-2-yl)-2H-Piran-2-it.

Example 292. 4 atomic charges-3,5-dimethyl-6-(6-methoxyethoxymethyl-2-yl)-2H-Piran-2-it.

Example 293. 6-(5-carboxybenzene-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-it.

Example 294. 4 atomic charges-3,5-dimethyl-6-(5-(phenoxycarbonyl)benzofuran-2-yl)-2H-Piran-2-it.

Example 295. 4 atomic charges-3,5-dimethyl-6-(5-(phenylcarbamoyl)benzofuran-2-yl)-2H-Piran-2-it.

Example 296. 4 atomic charges-6-(5-benzyloxybenzophenone-2-yl)-3,5-dimethyl-what-2H-Piran-2-it.

Example 298. 3,5-dimethyl-4-hydroxy-6-(5-(N-methyl-N-phenylsulfonyl)benzofuran-2-yl)-2H-Piran-2-it.

Example 299. 3,5-dimethyl-4-hydroxy-6-(5-(N-methyl-N-phenylcarbamoyl)benzofuran-2-yl)-2H-Piran-2-it.

Example 300. 6-(5-(benzimidazolecarbamic)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-it.

Example 301. 6-(5-(benzothiazolylthio)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-it.

Example 302. 3,5-dimethyl-4-hydroxy-6-(5-(1,3,4-trihydroxyphenyl-2-ylcarbonyl)benzofuran-2-yl)-2H-Piran-2-it.

Example 303. 3,5-dimethyl-4-hydroxy-6-(5-morpholinomethyl-2-yl)-2H-Piran-2-it.

Example 304. 3,5-dimethyl-4-hydroxy-6-(5-(5-hydroxy-3-pyridyloxy)benzofuran-2-yl)-2H-Piran-2-it.

Example 305. 3,5-dimethyl-4-hydroxy-6-(5-(4-(sulfamoyl) phenylcarbamoyl)benzofuran-2-yl)-2H-Piran-2-it.

Example 306. 3,5-dimethyl-4-hydroxy-6-(5-(4-pyridylmethylene)benzofuran-2-yl)-2H-Piran-2-it.

Example 307. 3,5-dimethyl-4-hydroxy-6-(5-(4-piperidinyl) benzofuran-2-yl)-2H-Piran-2-it.

Example 308. 6-(5-(N-benzyl-N-methylcarbamoyl)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-it.

Example 309. 3,5-dimethyl-4-hydroxy-6-(5-(N-methyl-N-(4-pyridyl)carbarnoyl)benzofuran-2-yl)-2H-Piran-2-it.

Example 310
4cells per well and used 1 ml of medium (eRDF medium containing 10% bovine serum (Kyokuto Chemical Co.)) for a 6-day cultivation in the presence of 5% CO2at 37oC. After removal supernatants environment of the cells were again washed with 1 ml of buffer solution PBS(-) (Takara Shuzo), which is then removed. This procedure was repeated twice, and then added 1 ml of fresh medium (eRDF environment).

Sample preparation

6-(benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he (Example 2) was dissolved in dimethyl sulfoxide (DMSO) to prepare the original sample solution with a concentration of 20 mm. The diluted solution was obtained by dilution of the original sample solution using DMSO.

Producing TG

To the cells, prepared as described above was added to the original or diluted sample solution 5 µl per well and 10 μl of solution14With-acetic acid (solution Amersham code No CFA13, diluted 4.4 times with buffer PBS(-), the cultivation was performed in one day in the presence of 5% CO2at 37oC.

Quantification TG

After the cultivation was completed, the culture solution was removed and added to 1 ml of extraction solution (n-hexane and isopropyl alcohol, tract, containing the obtained lipid components, dried in air, the residue was dissolved in 20 μl of a solution of n-hexane and ethyl acetate, mixed in the ratio of 9:1, this solution was put on a plate for thin-layer chromatography (S319, Tokyo Kasei), thin layer chromatography was carried out in the mixed solution mentioned above. After air drying, the lipid components were stained with iodine vapours and cut part of the plate corresponding to TG, the number obtained by biosynthesis of TG was measured using a liquid scintillation counter. The results are shown in Table 1. It was demonstrated that 6-(benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-it shows inhibitory activity against biosynthesis of triglycerides.

Example 311

Inhibitory activity of the compounds according to the invention in relation to the production of TG was evaluated in the same manner as in the example described above. According to the results of the evaluation of the compounds of examples with the following numbers have the value of the IC50less than 10 µm and showed at least 30% of inhibitory activity against the production of TG at a concentration of 1 μm or at least 50% inhibitory activity against the production of TG at a concentration of 10 µm:9, 97, 117, 120, 122, 134, 138, 153, 159, 163, 170, 215, 226, 228, 236, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 255, 257, 259, 260, 265, 268, 270, 271, 274, 285, 290, 291, 297, 298, 299, 300, 301, 302, 303, 304, 305, 306, 307, 308, 309.

Compounds of examples with the following numbers have the value of the IC50less than 10 microns and less than 100 μm and showed at least 5% and less than 30% of inhibitory activity against the production of TG at a concentration of 1 μm; or at least 30% and less than 50% of inhibitory activity against the production of TG at a concentration of 10 μm: 6, 7, 8, 14, 17, 18, 20, 22, 23, 24, 32, 35, 37, 38, 43, 46, 47, 60, 67, 68, 74, 79, 81, 83, 87, 95, 107, 115, 124, 126, 144, 155, 157, 175, 177, 179, 181, 183, 185, 187, 191,193, 195, 197, 201, 203, 207, 213, 217, 220, 222, 224, 230, 240, 253, 254, 258, 261, 262, 263, 264, 266, 267, 269, 272, 273, 275, 278, 280, 281, 282, 283, 284, 286, 287, 292, 295, 296.

Example 312. Test for the evaluation of medicinal effect

6-(benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-Piran-2-he (Example 2) suspended in 0.5% aqueous solution of the Na salt of carboxymethyl cellulose (solvent) to prepare a solution for injection to a concentration of 20 and 60 mg/ml, and this solution was administered orally to 6-week-old SD male rats in a dose of 5 ml/kg once daily for 7 consecutive days. CE-2 Nihon Crea Co. used for feeding of rats, and the rats had free access to food and water. Rats derstine tool. 4 hours after the last injection drug rats were killed using ether anesthesia, and then they took blood from abdominal aorta and measured the levels of serum TG, total cholesterol (TC) and HDL.

Test Wako on triglyceride EII-HA (a product of Wako Junyaku Coduo) used for the measurement of the TG, Test Wako on / Test Wako on cholesterol E (a product of Wako Junyaku Coduo) was used for measurement of total cholesterol (TC), Test Wako on HDL-cholesterol (product of Wako Junyaku Coduo) was used to measure the content of HDL.

As shown in Table 2, the group, which was administered compounds according to the invention had lower levels of TG, depending on the dosage. As shown in Table 3, the levels of TC and HDL were increased depending on the dosage. The increase in the content of CU is almost entirely consistent with the increase in the content of HDL. During the introduction of no deaths in rats or inhibiting the increase of body weight was not found.

The above data demonstrate that the compounds according to the invention have the effect of reducing the levels of TG and/or the effect of increasing levels of HDL, and they Bednogo exchange, as well as agents for the prevention of atherosclerosis or agents for the treatment of atherosclerosis.

Example 313

Tablets were prepared so that each tablet contained the following composition.

Active ingredient - 200 mcg

Lactose - 180 mg

Potato starch 50 mg

Polyvinylpyrrolidone 10 mg

Magnesium stearate 5 mg

The active ingredient, lactose and potato starch were combined and the mixture is evenly moistened 20% solution of polyvinylpyrrolidone in ethanol. The moistened mixture was passed through a 20 mesh molecular sieve, dried at 45oC and then passed through a 15 mesh molecular sieve. Thus obtained granules were mixed with magnesium stearate and compressed into tablets.

Example 314

Hard gelatin capsules were prepared so that each capsule contained the following composition.

Active ingredient - 100 mcg

Thin crystalline cellulose - 195 mg

Amorphous silicic acid 5 mg

The active ingredient, fine crystalline cellulose and nepressovannaya amorphous silicic acid were thoroughly mixed and placed in hard gelatin capsules.

Example 315

The active ingredient was dissolved in fraction is; what the objects of study were the installation, producing soft capsules, for the preparation of soft capsules according to the usual technique: 100 micrograms of active ingredient per capsule.

The coating composition weight.h.:

Gelatin - 10

Glycerin - 5

Sorbic acid - 0,08

Purified water - 14

Industrial applicability

The pharmaceutical agents of the present invention exhibit inhibitory activity against biosynthesis of triglycerides, as well as have the effect of reducing the level of triglycerides in the blood, or the effect of increasing the levels of HDL in the blood, and they can therefore be used as therapeutic agents in hypertriglyceridemia, amplifiers lipid metabolism or as agents for prevention and/or treatment of atherosclerosis.

1. The derived benzofuran--Piron, represented by the following structural formula (I)

< / BR>
where R1represents a hydrogen or alkyl group containing from 1 to 5 carbon atoms;

R2represents hydrogen, -CO-R5(where R5represents hydrogen, alkyl group containing from 1 to 5 carbon atoms, optionally containing substituents, cycloalkyl group, with the UB>2
R6(where R6represents an alkyl group containing from 1 to 5 carbon atoms, optionally substituted with halogen, or aryl group containing from 6 to 10 carbon atoms);

R3represents hydrogen, alkyl group containing from 1 to 5 carbon atoms, alkenylphenol group containing from 2 to 5 carbon atoms, alkylamino group containing from 2 to 5 carbon atoms, cycloalkyl group containing from 3 to 7 carbon atoms, cycloalkyl group containing from 3 to 7 carbon atoms alkyl group containing from 1 to 5 carbon atoms, aryl group containing from 6 to 10 carbon atoms, aracelio group containing from 7 to 20 carbon atoms, alkoxygroup, containing from 1 to 5 carbon atoms, or alloctype containing from 6 to 10 carbon atoms;

R4is a substituent at C-4 position, 5-position, 6-position or the C-7 position benzofuranol ring and represents:

R4Athat represents a hydrogen, a nitro-group, a cyano, a halogen atom, a heterocycle, alkenylphenol group containing from 2 to 5 carbon atoms, alkylamino group containing from 2 to 5 carbon atoms, aryl group containing from 6 to 10 atoms awaynow bond and n represents 0, 1 or 2), A=CH(CH2)mO- (where a represents the alicyclic heterocycle, "=" represents a double bond, and m represents 1, 2 or 3), A-SO2-(CH2)m- (where a represents a heterocycle alicyclic and m represents 1, 2 or 3), -OR7(where R7represents hydrogen, cycloalkyl group containing from 3 to 7 carbon atoms, aryl group containing from 6 to 10 carbon atoms, a heterocycle, or alkylsulfonyl group containing from 1 to 4 carbon atoms, optionally substituted with halogen, or arylsulfonyl group containing from 6 to 10 carbon atoms), -O-CO-R8(where R8represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, aryl group containing from 6 to 10 carbon atoms, aracelio group containing from 7 to 20 carbon atoms, or a heterocycle), -NR9R10(where each of R9and R10independently represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, aracelio group containing from 7 to 20 carbon atoms, a heterocycle, phenyl group, -SO2-R11(where R11represents optionally substituted with halogen alkyl group, containing the ing group, containing from 6 to 10 carbon atoms, a heterocycle or aracelio group containing from 7 to 20 carbon atoms) or-CO-R12(where R12represents hydrogen, alkyl group containing from 1 to 12 carbon atoms, aryl group containing from 6 to 10 carbon atoms, aracelio group containing from 7 to 20 carbon atoms, a heterocycle, alkoxygroup containing from 1 to 10 carbon atoms, substituted heterocycle alkyl group containing from 1 to 6 carbon atoms, alloctype containing from 6 to 10 carbon atoms, heterokaryosis or aralkylated containing from 7 to 20 carbon atoms)), -CO-R13(where R13represents hydrogen, -HE, the alkyl group containing from 1 to 4 carbon atoms, aryl group containing from 6 to 10 carbon atoms, a heterocycle, alkoxygroup containing from 1 to 4 carbon atoms, alloctype containing from 6 to 10 carbon atoms, or aralkylated containing from 7 to 20 carbon atoms), or-CO-NR14R15(where each of R14and R15independently represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, cycloalkyl group containing from 3 to 7 carbon atoms, aryl group containing from 6 to 10 clam alkyl group, containing from 1 to 4 carbon atoms);

R4bthat represents a saturated or unsaturated alkoxygroup containing from 1 to 6 carbon atoms, optionally substituted by 1-3 groups selected from the group consisting of halogen, cycloalkyl groups containing from 3 to 7 carbon atoms, phenyl, naphthyl, heterocycle, -OR16(where R16represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, phenyl group, naftalina group, benzyl group, or a heterocycle), -O-CO-R16(where R16represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, phenyl group, naftalina group, benzyl group, or a heterocycle), -NR17R18(where each of R17and R18independently represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, a heterocycle, alkylsulfonyl group containing from 1 to 4 carbon atoms, phenylsulfonyl group, -SO2-Het where Het represents a heterocycle), aminosulfonyl group, methylaminomethyl group, dimethylaminomethyl group, diethylaminomethyl group or alkyl group containing from 1 to 4 carbon atoms, substituted one of hydroxyl, -NH-CO-R19(where R19represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, phenyl group, naftalina group, a benzyl group, a heterocycle, alkoxygroup containing from 1 to 4 carbon atoms, or benzyloxy), -CO-R20(where R20represents hydrogen, heterocycle, alkoxygroup containing from 1 to 4 carbon atoms, fenoxaprop, benzyloxy or21(where R21represents hydrogen or a heterocycle), and-CO-NR22R23(where each of R22and R23independently represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, benzyl group or a heterocycle); or

R4cthat represents an alkyl group containing from 1 to 4 carbon atoms, optionally substituted by 1-3 groups selected from the group consisting of halogen, cycloalkyl groups containing from 3 to 7 carbon atoms, phenyl, naphthyl, heterocycle, -SH, -OR16(where R16represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, phenyl group, naftalina group, benzyl group, or a heterocycle), -O-CO-R16(where R16represents hydrogen, alkyl group containing about what 8 (where each of R17and R18independently represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, a heterocycle, alkylsulfonyl group containing from 1 to 4 carbon atoms, phenylsulfonyl group, -SO2-Het where Het represents a heterocycle), aminosulfonyl group, methylaminomethyl group, dimethylaminomethyl group, diethylaminomethyl group or alkyl group containing from 1 to 4 carbon atoms, substituted by one or two groups selected from phenyl, heterocyclic compounds, phenoxy, -O-Het where Het represents a heterocycle), and hydroxyl, -NH-CO-R19(where R19represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, phenyl group, naftalina group, a benzyl group, a heterocycle, alkoxygroup containing from 1 to 4 carbon atoms, or benzyloxy group), -CO-R20(where R20represents hydrogen, heterocycle, alkoxygroup containing from 1 to 4 carbon atoms, fenoxaprop, benzyloxy or21(where R21represents hydrogen or a heterocycle), and-CO-NR22R23(where each of R22and R23independently represents hydrogen, alkyl group, with Achyut provisions in benzofuranol ring;

or its salt.

2. The derived benzofuran--Piron under item 1, wherein R1represents hydrogen, methyl, ethyl or isopropyl; or its salt.

3. The derived benzofuran--Piron under item 1, wherein R1represents methyl; or its salt.

4. The derived benzofuran--Piron according to any one of paragraphs.1-3, wherein R5represents (1) an alkyl group containing from 1 to 5 carbon atoms, optionally substituted by 1-4 substituents selected from the group consisting of halogen, -OR8(where R8represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, aryl group containing from 6 to 10 carbon atoms, aracelio group containing from 7 to 20 carbon atoms, or a heterocycle), -O-CO-R8(where R8represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, aryl group containing from 6 to 10 carbon atoms, aracelio group containing from 7 to 20 carbon atoms, or a heterocycle), -NR9R10(where each of R9and R10independently represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, aracelio group containing from 7 to 20 is about 4 carbon atoms, or arylsulfonyl group containing from 6 to 10 carbon atoms), -NH-CO-R24(where R24represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, aryl group containing from 6 to 10 carbon atoms, aracelio group containing from 7 to 20 carbon atoms, a heterocycle, alkoxygroup containing from 1 to 4 carbon atoms, or urlcategory containing from 7 to 20 carbon atoms), cycloalkyl groups containing from 3 to 7 carbon atoms, aryl groups containing from 6 to 10 carbon atoms, heterocycles and-CO-R25(where R25represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, a heterocycle, OR8(where R8represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, aryl group containing from 6 to 10 carbon atoms, aracelio group containing from 7 to 20 carbon atoms, or a heterocycle), or-NR26R27(where each of R26and R27independently represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, aracelio group containing from 7 to 20 carbon atoms or a heterocycle)), (2) hydrogen atom, (3) cycloalkyl group containing from 3 to 7 carbon atoms, (4) aryl EIL--Piron according to any one of paragraphs.1-3, wherein R5represents (1) an alkyl group containing from 1 to 5 carbon atoms, optionally substituted by 1-3 substituents selected from the group consisting of HE, alkoxygroup containing from 1 to 4 carbon atoms, phenoxy, benzyloxy, -O-CO-R28(where R28represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, phenyl group or a heterocycle), -NR29R30(where each of R29and R30independently represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, a benzyl group, a heterocycle or optionally substituted with halogen alkylsulfonyl group containing from 1 to 4 carbon atoms), -NH-CO-R31(where R31represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, a heterocycle, alkoxygroup containing from 1 to 4 carbon atoms, or benzyloxy), aryl groups containing from 6 to 10 carbon atoms, heterocycles and-CO-R32(where R32represents hydrogen, O-R32(where R32represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, benzyl group or a heterocycle), -NR33R34(where each of R33and R34snesapu, containing from 3 to 7 carbon atoms, (3) aryl group containing from 6 to 10 carbon atoms, or (4) a heterocycle; or its salt.

6. The derived benzofuran--Piron according to any one of paragraphs.1-3, wherein R5represents (1) an alkyl group containing from 1 to 5 carbon atoms, optionally substituted by 1-3 substituents selected from the group consisting of phenoxy, -NR29R30(where each of R29and R30independently represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, a benzyl group, a heterocycle or optionally substituted with halogen alkylsulfonyl group containing from 1 to 4 carbon atoms), -NH-CO-R31(where R31represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, a heterocycle, alkoxygroup containing from 1 to 4 carbon atoms or benzyloxy), phenyl and-CO-R35(where R35is a HE, alkoxygroup containing from 1 to 4 carbon atoms, benzyloxy, -NR33R34(where each of R33and R34independently represents hydrogen, methyl, ethyl, benzyl or a heterocycle or a heterocycle), (2) aryl group containing from 6 to 10 carbon atoms, or (3) geteroseksualist a (1) alkyl group, containing from 1 to 5 carbon atoms, optionally substituted by 1 or 2 substituents selected from the group consisting of phenoxy, -NR36R37(where each of R36and R37independently represents hydrogen or methyl), -NH-CO-R38(where R38represents hydrogen, methyl, heterocycle, tert.-butoxy or benzyloxy, phenyl and-CO-R39(where R39represents a heterocycle), (2) phenyl group, or (3) a heterocycle; or its salt.

8. The derived benzofuran--Piron according to any one of paragraphs.1-7, wherein R2represents hydrogen or-CO-R5; or its salt.

9. The derived benzofuran--Piron according to any one of paragraphs.1-3, wherein R2represents hydrogen, acetyl, isobutyryl, benzoyl, 4-methoxybenzoyl, 2,4-dimethoxybenzoyl, 4-hydroxymethylbenzene, 3-dimethylaminobenzoyl, 4-acetylaminobenzoic, phenylacetyl, 3-phenylpropionyl, phenoxyacetyl, furan-2-carbonyl, pyridine-4-carbonyl, pyridine-3-carbonyl, pyridine-2-carbonyl, 6-hydroxypyridine-3-carbonyl, 2-aminoacetyl, 2-(tert.-butoxycarbonylamino)acetyl, 2-(N-carbobenzoxy-N-methylamino)acetyl, 1-carbobenzoxy-2-pyrrolidone-5-carbonyl, 2-pyrrolidone-5-carbonyl, 3-acetylamino-4-morpholinyl-4-oxobutyl is any of paragraphs.1-3, wherein R2represents hydrogen or acetyl; or its salt.

11. The derived benzofuran--Piron according to any one of paragraphs.1-10, wherein R3represents hydrogen, alkyl group containing from 1 to 5 carbon atoms, alkenylphenol group containing from 2 to 5 carbon atoms, alkylamino group containing from 2 to 5 carbon atoms, 2-cycloalkylation group containing from 4 to 8 carbon atoms, cycloalkylation group containing from 5 to 9 carbon atoms, phenyl group, benzyl group, fenetylline group, methoxy group, or fenoxaprop; or its salt.

12. The derived benzofuran--Piron according to any one of paragraphs.1-10, wherein R3represents hydrogen, alkyl group containing from 1 to 5 carbon atoms, alkenylphenol group containing from 2 to 4 carbon atoms, cycloalkenyl group containing 6 to 7 carbon atoms, 2-cycloalkylation group containing 7 to 8 carbon atoms, phenyl group, benzyl group, a methoxy group or fenoxaprop; or its salt.

13. The derived benzofuran--Piron according to any one of paragraphs.1-10, wherein R3represents an alkyl group containing about what Eesa fact, what R3represents methyl or ethyl; or its salt.

15. The derived benzofuran--Piron according to any one of paragraphs.1-14, wherein R4crepresents an alkyl group containing from 1 to 3 carbon atoms, optionally substituted by 1-3 substituents selected from the group consisting of heterocycles, -SH, -HE, alkoxy groups containing from 1 to 4 carbon atoms, acyloxy containing from 1 to 4 carbon atoms, -NR40R41(where each of R40and R41independently represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, optionally substituted with halogen alkylsulfonyl group containing from 1 to 4 carbon atoms, or alkyl group containing 1 or 2 carbon atoms, substituted by 1 or 2 substituents selected from phenyl, heterocyclic compounds, phenoxy, -O-Het where Het represents a heterocycle), and hydroxyl), -NH-CO-R42(where R42represents hydrogen, phenyl, alkyl group containing from 1 to 4 carbon atoms, or alkoxygroup containing from 1 to 4 carbon atoms), -CO-R43(where R43represents hydrogen, heterocycle, alkoxygroup containing from 1 to 4 carbon atoms, or21(where R21is sababoy hydrogen, alkyl group containing from 1 to 4 carbon atoms, or a heterocycle); or its salt.

16. The derived benzofuran--Piron according to any one of paragraphs.1-14, wherein R4crepresents an alkyl group containing from 1 to 3 carbon atoms, substituted heterocycle, -SH, benzoylamine, allmineral containing from 1 to 5 carbon atoms, or-NR40R41(where each of R40and R41independently represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, optionally substituted with halogen alkylsulfonyl group containing from 1 to 4 carbon atoms, or alkyl group containing 1 or 2 carbon atoms, substituted by 1 or 2 substituents selected from phenyl, heterocyclic compounds, phenoxy, -O-Het where Het represents a heterocycle), and hydroxyl); or its salt.

17. The derived benzofuran--Piron according to any one of paragraphs.1-14, wherein R4crepresents (3,5-dioxo-2,4-thiazolidine)methyl, (3,5-dioxo-2,4-oxazolidinyl)methyl or (5-oxo-3-thioxo-2,4-thiazolidine)methyl; or its salt.

18. The derived benzofuran--Piron according to any one of paragraphs.1-14, wherein R4crepresents (3,5-dioxo-2,4-thiazolidine)methyl; or its salt.

2N, alkoxycarbonyl groups containing from 2 to 5 carbon atoms, -OR46(where R46represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, phenyl group, benzyl group, or a heterocycle), and-NR47R48(where each of R47and R48independently represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, alkoxycarbonyl group containing from 2 to 5 carbon atoms, a heterocycle, alkylsulfonyl group containing from 1 to 4 carbon atoms, phenylsulfonyl group, -SO2-Het where Het represents a heterocycle), aminosulfonyl group, methylaminomethyl group, dimethylaminomethyl group, diethylaminomethyl group, acyl group containing from 1 to 5 carbon atoms, benzoyloxy group, -CO-Het where Het represents a heterocycle), benzyloxycarbonyloxy group or alkyl group containing from 1 to 4 atoms of second heterocycle) and hydroxyl) or unsaturated alkoxygroup, containing from 3 to 6 carbon atoms; or its salt.

20. The derived benzofuran--Piron according to any one of paragraphs.1-18, wherein R4brepresents methoxy, 2-propenyloxy, 2,2-DIMETHYLPROPANE, cyclopentyloxy, 2-bromoethoxy, benzyloxy, Chlorobenzilate, fermentelos, (trifluoromethyl)benzyloxy, DICHLOROSILANE, dimethylbenzylamine, methoxybenzyloxy, sulfamoylbenzoic (methylendioxy)benzyloxy, carboxymethoxy, (ethoxycarbonyl)benzyloxy, n-butoxybenzoate, aminobenzoate, (tert.-butoxycarbonylamino)benzyloxy, 3-phenylpropoxy, di(methoxyphenyl)methoxy, 1-methyl-1-phenylethane, aftermarket, titillate, 2-(morpholinomethyl)titillate, pyridyloxy, (2-methoxyphenyl)methoxy, 2-(pyridyl)ethoxy, personalitati, pyrimidinylidene, oxazolidinone, 4-phenyloxazolidine, imidazolidinone, 3-tosyl-5-methylimidazolidine, thiazoleacetate, 4-methyldiethanolamine, 2-(morpholinomethyl)thiazoleacetate, 2,4-Dichlorotoluene, 2-(5-thiazolyl)ethoxy, 2-(4-methyl-5-thiazolyl)ethoxy, (3,5-dioxo-2,4-thiazolidine)methoxy, N-methylpiperidine, (4-archroma-2-yl)methoxy, (3,3-dimethyl-2,4-DIOXOLANYL)methoxy, methoxymethyl, 2-(atomic charges)ethoxy, bis(dimethylaminomethyl)pentyloxy or 2-(benzyloxy)ethoxy; or its salt.

21. The derived benzofuran--Piron according to any one of paragraphs.1-18, wherein R4brepresents methoxy, 2-propenyloxy, benzyloxy, Chlorobenzilate, fermentelos, (trifluoromethyl)benzyloxy, DICHLOROSILANE, dimethylbenzylamine, methoxybenzyloxy, sulfamoylbenzoic (methylendioxy)benzyloxy, carboxymethoxy, (ethoxycarbonyl)benzyloxy, n-butoxybenzoate, aminobenzoate, (tert.-butoxycarbonylamino)benzyloxy, titillate, 2-(morpholinomethyl)titillate, pyridyloxy, (2-methoxyphenyl)methoxy, 2-(pyridyl)ethoxy, personalitati, pyrimidinylidene, oxazolidinone, 4-phenyloxazolidine, imidazolidinone, 3-tosyl-5-methylimidazolidine, thiazoleacetate, 4-methyldiethanolamine, 2-(morpholinomethyl)thiazoleacetate, 2,4-Dichlorotoluene, 2-(5-thiazolyl)ethoxy, 2-(4-methyl-5-thiazolyl)ethoxy, (3,5-dioxo-2,4-thiazolidine)methoxy, N-methylpiperidine or methoxymethyl; or its salt.

22. The derived benzofuran--Piron according to any one of paragraphs.1-21, wherein R4arepresents hydrogen, a nitro-group, a cyano, a halogen atom, a heterocycle, A=CH(CH2)n- (where a is an alicyclic heterocy is employed, an alicyclic the heterocycle, "= " is a double bond, and m represents 1, 2 or 3), A-SO2(CH2)m- (where a represents a heterocycle alicyclic and m represents 1, 2 or 3), -OR49(where R49represents hydrogen, a heterocycle, optionally substituted with halogen alkylsulfonyl group containing from 1 to 4 carbon atoms, or phenylsulfonyl group), -O-CO-R50(where R50represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, or phenyl), -NR51R52(where each of R51and R52independently represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, phenyl, benzyl, -S02-R53(where R53represents phenyl, naphthyl, heterocycle or alkyl group containing from 1 to 3 carbon atoms, optionally substituted by 1-3 substituents selected from the group consisting of halogen atoms, heterocycles or phenyl), or-CO-R54(where R54represents hydrogen, phenyl, naphthyl, heterocycle, alkoxygroup containing from 1 to 4 carbon atoms, fenoxaprop, naphthyloxy, heterokaryosis, aralkylated group containing from 7 to 11 carbon atoms, or alkyl group containing from 1 det a hydrogen, HE, heterocycle, alkoxygroup containing from 1 to 4 carbon atoms, or fenoxaprop), or-CO-NR56R57(where each of R56and R57independently represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, cycloalkyl group containing from 3 to 7 carbon atoms, phenyl group, benzyl group, fenetylline group, a heterocycle or substituted heterocycle alkyl group containing from 1 to 4 carbon atoms); or its salt.

23. The derived benzofuran--Piron according to any one of paragraphs.1-21, wherein R4arepresents hydrogen, a nitro-group, a cyano, a halogen atom, a heterocycle, A=CH(CH2)n- (where a represents the alicyclic heterocycle, "= " represents a double bond and n represents 0, 1 or 2), A=CH(CH2)mO- (where a represents the alicyclic heterocycle, "= " represents a double bond, and m represents 1, 2 or 3), A-SO2(CH2)m- (where a represents a heterocycle alicyclic and m represents 1, 2 or 3), -OR53(where R58represents hydrogen, optionally substituted by halogen alkylsulfonyl group containing from 1 to 4 carbon atoms, ildo 4 carbon atoms, or phenyl), -NR60R61(where each of R60and R61independently represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, phenyl, benzyl, -SO2-R62(where R62represents optionally substituted with halogen alkyl group containing from 1 to 3 carbon atoms, substituted heterocycle alkyl group containing from 1 to 3 carbon atoms, phenyl group, a heterocycle, a benzyl group or fenetylline group), or-CO-R63(where R63represents an alkyl group containing from 1 to 4 carbon atoms, phenyl group, aracelio group containing from 7 to 9 carbon atoms, a heterocycle, alkoxygroup containing from 1 to 4 carbon atoms, substituted heterocycle alkyl group containing from 1 to 3 carbon atoms, fenoxaprop, heterokaryosis or benzyloxy)), -CO-R64(where R64represents hydrogen, -HE or alkoxygroup containing from 1 to 4 carbon atoms), or-CO-NR65R66(where each of R65and R66independently represents hydrogen, alkyl group containing from 1 to 4 carbon atoms, cycloalkyl group containing from 3 to 7 carbon atoms, phenyl group, benzylation carbon); or its salt.

24. The derived benzofuran--Piron according to any one of paragraphs.1-21, wherein R48represents hydrogen, nitro, cyano, bromine, thiazolyl, furyl, thienyl, morpholinyl, piperazinil, hydroxyl, methansulfonate, tripterocalyx, vinylsulfonate, atomic charges, benzoyloxy, dimethylamino, dibenzylamino, phenylcarbonylamino, dimethylcarbamoyl, N-methyl-N-phenylcarbamoyl, N-benzyl-N-methylcarbamoyl, cyclohexylcarbonyl, phenylcarbamoyl, imidazolylalkyl, benzimidazolecarbamic, thiazolecarboxamide, benzothiazolylthio, isothiazolinones, personalberater, triazolylmethyl, pyridylcarbinol, pyrimidinecarbonitrile, pyrazinecarboxamide, isoxazolecarboxylic, formyl, carboxyl, methoxycarbonyl, etoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, tert.-butoxycarbonyl, acetyl, benzoyl, 1,3,4-trihydroxyphenyl-2-ylcarbonyl, (3,5-dioxo-2,4-thiazolidinedione)methyl, (3,5-dioxo-2,4-oxazolidinedione)methyl, (2,5-dioxoimidazolidin-4-ilidene)methyl, (5-oxo-3-thioxo-2,4-thiazolidinedione)methyl, ((3,5-dioxo-2,4-thiazolidine)sulfonyl)methyl, ((3,5-dioxo-2,4-oxazolidinyl)sulfonyl) methyl, ((2,5-dioxoimidazolidin-4-yl)sulfonyl)methyl, ((5-oxo-3-thioxo-2,4-thiazolidine) with whom to 4 carbon atoms, and R68represents an alkyl group containing from 1 to 3 carbon atoms, phenyl group, a heterocycle, aracelio group containing from 7 to 9 carbon atoms, or alkoxygroup containing from 1 to 4 carbon atoms); or its salt.

25. The derived benzofuran--Piron according to any one of paragraphs.1-21, wherein R4arepresents hydrogen, nitro, cyano, bromine, thienyl, piperazinil, hydroxyl, tripterocalyx, vinylsulfonate, atomic charges, dimethylamino, dibenzylamino, thiazolecarboxamide, methoxycarbonyl, isopropoxycarbonyl, (3,5-dioxo-2,4-thiazolidinedione) methyl, or-N(Me)-CO-R69(where R69represents an alkyl group containing from 1 to 3 carbon atoms, phenyl group, a heterocycle, a benzyl group, or alkoxygroup containing from 1 to 4 carbon atoms); or its salt.

26. Pharmaceutical composition having inhibitory activity against the production of TG, comprising a therapeutically effective dose derived benzofuran--Piron according to any one of paragraphs.1-25 or its salt and a pharmaceutically acceptable carrier.

27. The amplifier lipid metabolism, comprising as an active ingredient derived benzofuran--Piron the active ingredient derived benzofuran--Piron according to any one of paragraphs.1-25 or its salt.

29. The agent reducing triglycerides in the blood, comprising as an active ingredient derived benzofuran--Piron according to any one of paragraphs. 1-25 or its salt.

30. Agent, increase the content of HDL, comprising as an active ingredient derived benzofuran--Piron according to any one of paragraphs.1-25 or its salt.

31. The agent for the prevention of atherosclerosis, comprising as an active ingredient derived benzofuran--Piron according to any one of paragraphs.1-25 or its salt.

32. Agent for treatment of atherosclerosis, comprising as an active ingredient derived benzofuran--Piron according to any one of paragraphs.1-25 or its salt.

 

Same patents:

The invention relates to the derivatives of pyrrolidine formula I

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where R1- H, C1-C6alkyl; phenyl, possibly substituted; biphenyl, possibly substituted; 1H, 5H - pyrido [3,2,1-ij] chinolin; phenyl WITH1-C6alkyl, optionally substituted; biphenyl WITH1-C6alkyl, optionally substituted; biphenylcarboxylic; terphenyl; naphthyl, optionally substituted; Z denotes-S-, -O-, -och2-, -N(R16), where R16- H, C1-C6alkyl, C3-C8cycloalkyl1-C6alkyl, panels1-C6alkyl, a chemical bond; X1means-CO-, -(CH2)r-CO-N(R17), where R17means H, C1-C6alkyl (where r = 0 or 1), -CH2NHSO2-, -(CH2)s-N (R18)-CO- (where R18- N, s=1-3), - CH2NHCОСН2O-, -CH2N (R19Of PINES = CH- (where R19- H, -CH2OCH2-, -CH2-N (R20)-CH2- (where R20- H, C1-C6alkyl, C1-C6alkylsulphonyl, phenylcarbinol)1-C5alkylen,2-C4albaniles, a chemical bond; X2- phenylene, optionally substituted hydroxy, theoffender, purandar, piperidinyl,< / BR>
< / BR>
< / BR>
R2and R3each - H; and R4- phenyl, possibly substituted with halogen; R5- phenyl, possibly substituted; a cycle of G is phenyl,3-C7cycloalkyl, pyridyl, thienyl; loop J is phenyl; L is phenyl; p=0-2;----- means the presence or absence of chemical bonding;displays a CIS - or TRANS-configuration D relative to E; provided that X1means-CH2NHCО-, X2means 1,4-phenylene and X3means a chemical bond or a C1-C5alkylen, when the carbon atom bound CD and adjacent carbon atom in the cycle are connected by a simple relation and V1does not mean a chemical bond, when X1means-CH2O-; and pharmaceutically acceptable salt or hydrate of the compound

The invention relates to a method for the preparations of thiazolidinediones of the formula III, where a denotes CH=CH or S, W is O; X Is S, O or NR2where the remainder R2is hydrogen or C1-C6by alkyl; Y is CH or N; R is naphthyl, thienyl or phenyl, which optionally one - or twofold substituted C1-C3the alkyl, CF3C1-C3alkoxygroup, F, Cl or bromine; R1is hydrogen, C1-C6alkyl and n = 1-3, by restoring the compounds of formula IV metal aluminum in proton solvent

The invention relates to new derivatives of 2-(1,2,4-triazole-1-yl)-1,3,4-thiadiazole of the formula I, in which R1means a hydrogen atom, a C1-4alkyl group or phenyl group which may be substituted by 1 to 3 substituents selected from the group consisting of halogen atom, hydroxy-group, nitro group, WITH1-4alkoxygroup, (C1-4alkyl) amino and di(C1-4alkyl)amino group; or a group of formula (a) Z means a hydrogen atom or a C1-4alkoxygroup, R0means a group of the formula Alk-NR4R5where Alk is alkalinous group having a straight or branched C1-6chain, one of R2and R3is amino and the other is an amino group or a 5-6-membered saturated heterocyclic group containing one or two atom(s) of nitrogen and/or oxygen and attached via its nitrogen atom, and the specified heterocyclic group may be substituted WITH1-4alkyl group, phenyl group or kalogeropoulou group, or the last of the R2and R3is a group of the formula - SR

The invention relates to new bicyclic to carboxamide formula (i) in which (1) X represents N and (a) Z is =CR1-CR2and Y is N, Z is =CR1and Y represents O, S or NR4or (C) Z is = CR1-N= and Y represents CR2or (2), X represents NR4Z represents CR1= and Y is N, Q is O, R1and R2are СОR6, C(= NOR6R13, alkyl-C(=NOR6R13, NR8R9, CF3or R6, R3is1-6alkoxygroup, R4represents H or alkyl, R5is heteroaryl, optionally substituted with halogen, alkyl, CONR11R12, CF3or CN, aryl, substituted with halogen; R6represents H, alkyl, cycloalkyl, aryl, heteroaryl, heterocycle, arylalkyl, heteroaromatic or heteroseksualci, R7represents alkyl, hydroxy, OR10, NR8R9CN, CO2H, CO2R10, CONR11R12, R8and R9represent H or alkyl, or NR8R9represents a heterocyclic ring, optionally substituted by R14, R10represents an alkyl, heterocycle, R11and R12represent H or alkyl, and the salts

The invention relates to new derivatives of phenyloxazolidine that have a relationship with a 4-8-membered heterocyclic rings of formula I and their pharmaceutically acceptable salts, where X represents NR1, S(O)gor Oh, R1represents H, C1-6alkyl, optionally zamesheny one or more CN or halogen, -(CH2)h-phenyl, -COR1-1, -СООR1-2, -CO-(CH2)h-COR1-1, -SO2- C1-6alkyl or -(CO)i-Het, R2represents H, -CO-(C1-6)alkyl or fluorine, R3and R4are the same or different and represent H or halogen, R5is1-6alkyl and C3-6cycloalkyl, optionally substituted by one or more halogen, g=0, 1, or 2, h=1 or 2, i=0 or 1, m=0, 1, 2, 3, n= 0, 1, 2, 3, provided that m and n taken together, is equal to 1, 2, 3, 4 or 5

The invention relates to new compounds of the formula (I), where R1is (C3-C7)cycloalkyl group or a 3-7-membered saturated heterocyclic group containing 1 or 2 heteroatoms selected from nitrogen, oxygen, or sulfur, which may be optionally substituted by oxopropoxy; R2- aryl group, which optionally can be substituted by 1-3 halogen atoms; And a is methylene or carbonyl group; a simple bond; D is oxygen atom or sulfur; G is - (C1-C4)alkylenes group; L is a group of the formula-C(R4)(R5)-, where R4and R5defined in the claims, Z is two hydrogen atoms or an oxygen atom, n = 0 or 1, or its pharmaceutically acceptable salts, esters, Quaternary amines or hydrates

The invention relates to new carboxyterminal cyclic carboxamide derivative of formula 1

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where G1- CH2; G2- C(O); m = 2 or 3, n is 0 or 1; R1is 1-3 substituent, independently selected from H, G, C1-C6alkoxy; R2is 1-3 substituent, independently selected from H, C1-C6alkoxy; R3means N or

< / BR>
< / BR>
< / BR>
R4- H; Ar1means

< / BR>
< / BR>
R8means 1-3 substituent, independently selected from H, G; R9means N;

And means

< / BR>
< / BR>
< / BR>
where p = 1, 2, 3, or 4; X is-O-, -CH2-; R10-H, C1-C6alkyl or

< / BR>
">< / BR>
< / BR>
< / BR>
where q = 2 or 3; R5- C1-C4alkyl, (CH2)2HE; R6- C1-C4alkyl, -(CH2)2HE, (CH2)2N(CH3)2; R5', R6' - C1-C4alkyl; R7- C1-C6alkyl, and the stereoisomers and pharmaceutically acceptable salts

The invention relates to new isoxazol derivative of formula 1, where D represents hydrogen; one of a and b is a group (1) -E-N= C(NR25R26)NR27R28; E represents a direct link or alkilinity group; R25and R26each represents, independently, hydrogen; C1-4-alkyl; -(CH2)n-CO2R32, n is an integer of 1-3, and R32represents hydrogen, C1-4-alkyl; -(CH2)m-CO2R35m is 2 or 3 and R35represents hydrogen, C1-4-alkyl; -(CH2)mHE, m defined above, or -(CH2)n-C(O)R36n is defined above and R3represents hydrogen, C1-4-alkyl; and t

The invention relates to new derivatives of oxazolidinones General formula I, where R' denotes H, CN, Hal, or OA; R2, R3each independently of one another denotes H, CN, Hal, or2and R3together form methylenedioxy; And denotes alkyl with 1-6 C-atoms; Hal denotes F, Cl, Br, J; as well as their enantiomers and physiologically acceptable salts

The invention relates to new derivatives of kalaidjieva, fungicides, method of combating fungal diseases of crops and intermediate compounds for obtaining

The invention relates to new derivatives of piperidine-ketocarboxylic acids of the formula (I), where R1- COR4or SO2R4, R4means of alkenyl, substituted phenyl or pyridine, naphthyl, honokalani, chinoline, benzothiophene, dihydroxyphenyl or pyridyl, substituted with allmineral, R2- C1-C6-alkyl which can be substituted by phenyl or pyridium, R3group-OR6or other6where R6means hydrogen, C1-C6-alkyl, which may be a phenyl, pyridine or morpholinium, their tautomeric and isomeric forms, and salts

The invention relates to 1,4-disubstituted the piperazines of General formula I, the method of production thereof, containing compositions and their use for the clinical treatment of painful conditions, increased pain sensitivity and/or inflammatory conditions in which the pathophysiological role of C-fibers, causing neurogenic pain or inflammation

The invention relates to new derivatives of spirobiindane General formula (I), where R1represents a phenyl group which may be optionally substituted by 1-3 substituents selected from halogen atoms, lower alkyl groups, halogenized alkyl groups, lower alkoxygroup, lower alkoxycarbonyl groups, hydroxyl groups, lower aliphatic acylamino, cyano groups, or a 5 - or 6-membered heterocyclic group containing 1-3 oxygen atom, sulfur and/or nitrogen, which may be optionally condensed with a phenyl group; R2represents a phenyl group which is substituted by 1-3 fluorine atoms or chlorine; a represents a carbonyl group; represents a simple bond; D represents an oxygen atom or sulfur; E represents C1-4Allenova group;represents a group of formula (II), where G represents C5-8alonovoa ring, which is substituted by hydroxyl group; Ar represents a phenyl ring; n represents the integer 1 or 2, or a pharmacologically acceptable salt

The invention relates to new imidazole derivative of General formula (1), where n1is an integer from 1 to 3, a represents hydrogen, linear or branched C1-C10-alkyl, which may be optionally substituted C3-C7-cycloalkyl or lower alkoxy, or a radical selected from the group shown in the formula of the invention, Y represents a radical selected from the group described in the claims, or to his new pharmaceutically acceptable salts

The invention relates to new derivatives 7-[3-[4-(6-toranzo[d] isoxazol-3-yl)piperidine-1-yl] propoxy] -chromen-4-it formula I, where R is hydrogen, Cho, CH2OR2or COOH; R1means alkyl containing from 1 to 4 carbon atoms, provided that one of substituents R and R1is hydrogen, and their pharmaceutically acceptable salts, intended for use in the treatment of psychosis and schizophrenia, as well as to a method for producing these compounds, pharmaceutical compositions and method of inhibiting D2-, 5-HT2aand H1receptors in the treatment of psychosis and schizophrenia

The invention relates to new bicyclic to carboxamide formula (i) in which (1) X represents N and (a) Z is =CR1-CR2and Y is N, Z is =CR1and Y represents O, S or NR4or (C) Z is = CR1-N= and Y represents CR2or (2), X represents NR4Z represents CR1= and Y is N, Q is O, R1and R2are СОR6, C(= NOR6R13, alkyl-C(=NOR6R13, NR8R9, CF3or R6, R3is1-6alkoxygroup, R4represents H or alkyl, R5is heteroaryl, optionally substituted with halogen, alkyl, CONR11R12, CF3or CN, aryl, substituted with halogen; R6represents H, alkyl, cycloalkyl, aryl, heteroaryl, heterocycle, arylalkyl, heteroaromatic or heteroseksualci, R7represents alkyl, hydroxy, OR10, NR8R9CN, CO2H, CO2R10, CONR11R12, R8and R9represent H or alkyl, or NR8R9represents a heterocyclic ring, optionally substituted by R14, R10represents an alkyl, heterocycle, R11and R12represent H or alkyl, and the salts

The invention relates to new substituted derivatives of piperidine derivatives, to processes for their preparation, to pharmaceutical compositions and to their use in medical therapy, particularly in treatment of psychotic disorders
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