Fungicidal azocyclic amides

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of formula 1 and salts thereof, fungicidal compositions based on said compounds, a plant disease control method using compounds of formula , as well as intermediate compounds of formulae and . Values of radicals are given in the description.

EFFECT: high efficiency of the compounds.

14 cl, 20 dwg, 284 ex

 

The text descriptions are given in facsimile form.

1. A compound selected from formula 1, and its salt,

where R1represents phenyl, naphthalenyl or 5 - or 6-membered heteroaromatic ring, optionally substituted by 1-3 substituents, independently selected from R4aon ring carbon atoms and R4bon ring nitrogen atoms;
each R4aindependently represents a C1-C6alkyl, C1-C6halogenated, halogen, hydroxy, amino, cyano, C1-C4alkoxy, C1-C4halogenoalkane, C1-C4is kiltia, C1-C4allogenicity, C1-C4hydroxyalkyl or2-C6alkoxycarbonyl;
each R4bindependently represents a C1-C6alkyl;
But a CHR15or NH;
R15represents H, halogen, hydroxy, C1-C4alkyl, C2-C5alkoxycarbonyl or C1-C4alkoxy;
W represents O or S;
X represents a radical selected from

where are the connections in the X1X2or X3which is marked with the letter "t"attached to the carbon atom denoted by the letter "q" in formula 1, the bond which is marked with the letter "u"attached to the carbon atom denoted by the letter "r" in the formula 1, and a relationship that is marked with the letter "v"is connected to G;
each R2independently represents a C1-C4alkyl or hydroxy; or G represents a 5-membered heteroaromatic ring or 5-membered saturated or partially saturated heterocyclic ring, each ring optionally substituted up to 2 substituents selected from R3on ring carbon atoms and is selected from R11on ring nitrogen atoms;
each R3independently represents a C1-C3alkyl;
each R11independently represents a C1-C2al the sludge;
J is a 5-, 6 - or 7-membered ring, 8-11 membered bicyclic ring system or a 7 to 11-membered spirocyclic ring system, each ring or ring system containing ring members selected from carbon and optionally 1 to 4 heteroatoms selected from up to 2, O, up to 2 S and up to 4 N, and optionally includes from 1 to 3 ring members selected from the group consisting of C(=O), each ring or ring system optionally substituted by 1-5 substituents independently selected from R5;
each R5independently represents H, halogen, cyano, hydroxy, nitro, -NR25R26C1-C6alkyl, C2-C6alkenyl, C1-C6halogenated,2-C6halogenoalkanes,3-C8cycloalkyl,3-C8halogenosilanes,4-C10alkylsilanes,4-C10cycloalkenyl,2-C6alkoxyalkyl,2-C6alkylthiomethyl,2-C6alkylsulfonates,2-C6alkylsulfonates,2-C6alkylsulphonyl,2-C6alkoxycarbonyl, C1-C6hydroxyalkyl, C1-C6alkoxy, C1-C6halogenoalkane,3-C8cycloalkane,4-C10cycloalkylation,2-C6alkenylacyl, the 2-C6alkyloxy, C1-C6alkylthio, C1-C6allogenicity, C1-C6alkylsulfonyl or-Z2Q;
R25represents N or C1-C6alkyl;
R26represents a C1-C6alkyl or-Z4Q;
each Q independently represents a phenyl, benzyl, naphthalenyl, 5 - or 6-membered heteroaromatic ring or an 8 to 11-membered heteroaromatic bicyclic ring system, each optionally substituted by 1-5 substituents independently selected from R7to ring carbon atoms and R12for ring nitrogen atoms; or
each Q independently represents a 3-7-membered nonaromatic carbocyclic ring, a 5-, 6 - or 7-membered nonaromatic heterocyclic ring or an 8 to 11-membered nonaromatic bicyclic ring system, each ring optionally includes members selected from the group consisting of C(=O), and S(O)2and optionally substituted by 1-5 substituents independently selected from R7to ring carbon atoms and R12for ring nitrogen atoms;
each R7independently represents a C1-C6alkyl, C2-C6alkenyl,3-C6cycloalkyl,4-C10cycloalkenyl,4-C10alkylsilanes, C1-C6halogenated,2-C 6halogenoalkanes,3-C6halogenosilanes, halogen, hydroxy, cyano, nitro, C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4allogenicity, C2-C4alkoxyalkyl, C2-C5alkylsulphonyl,2-C6alkoxycarbonyl or2-C6alkylcarboxylic; or
when R5and R7taken together with the atoms linking R5and R7education optionally substituted 5-7-membered ring containing ring members selected from carbon and optionally 1 to 3 heteroatoms selected from up to 1 O, up to 1 S and up to 1 N, and optionally including 1 to 3 ring members selected from the group consisting of C(=O), and S(O)2ring, optionally substituted on ring members other than the atoms linking R5and R7in up to 4, substituents selected from R8;
each R8independently represents a C1-C6alkyl;
R12represents H, C1-C3alkyl, C2-C3alkylsulphonyl,1-C3alkoxy or2-C3alkoxycarbonyl;
Z1represents a direct bond or CH2;
each Z2Nezavisimosty a direct link, Oh, S(=O), S(O)m, CHR20or NR21;
each Z4represents C(=O);
each R20independently represents H, C1-C4alkyl or C1-C4halogenated;
each R21independently represents N or C1-C6alkylsulphonyl;
each m is 2; and
n is 0 or 1;
provided that:
(a) when R1represents an unsubstituted thienyl, X represents the X1and the ring containing X is saturated, G is an unsubstituted thiazole ring connected at its 2-position to X and at its 4-position to Z' in the formula 1, And represents CHR15, R15represents H and J represents isoxazole ring connected at its 4-position to Z1and substituted at its 5-position of the stands and at its 3-position, meta-substituted phenyl, then Z1represents CH2;
(b) when a represents NR16X is a X1or X2, Z1represents a direct bond, and J is a phenyl, then J is substituted by at least one of R5other than H, F, Cl, CN, co3, CF3and CH3.

2. The compound according to claim 1, where
G is a




where connection is projected to the left, attached to X, and bond, projected to the right, attached to the Z1;
J is a




where the connection is shown, projected to the left, attached to the Z1;
Q is a






R' represents a


each R3aindependently selected from H and R3;
each R5independently represents H, cyano, C1-C6alkyl, C2-C6alkenyl, C2-C6halogenated,2-C6halogenoalkanes,3-C8cycloalkyl,3-C8halogenosilanes,4-C10alkylsilanes,4-C10cycloalkenyl,2-C6alkoxyalkyl,2-C6alkylthiomethyl,2-C6alkoxycarbonyl, C1-C6alkoxy, C1-C6halogenoalkane,3-C8cycloalkane,4-C10cycloalkylation,3-C6alkenylacyl,3-C6alkyloxy, C1-C61-C6allogenicity, -NR25R26or Z2Q;
R11aselected from N and R11;
R15represents H, hydroxy, methyl or methoxycarbonyl;
k is 0, 1 or 2;
p is 0, 1, 2 or 3; and
x is an integer from 0 to 5;
provided that:
(a) when R4attached to the ring carbon atom specified R4selected from R4a;
(b) when R4attached to the ring nitrogen atom (for example, in U-4, U-11 To U-15, inclusive, U-24 U-26, inclusive, U-31 or U-35), the specified R4selected from R4b;
(c) when G is a G-6, G-16 or G-42, and each R3ais other than H, then R11arepresents H; and
(d) when G is a G-25 or G-31, then at least one R3arepresents N.

3. The compound according to claim 2, where
G is selected from G-1, G-2, G-7, G-8, G-14, G-15, G-23, G-24, G-26, G-27, G-36, G-37, G-38, G-49, G-50 and G-55;
J is selected from J-1, J-2, J-3, J-4, J-5, J-7, J-8, J-9, J-10, J-11, J-12, J-14, J-15, J-16, J-20, J-24, J-25, J-26, J-29, J-30, J-37, J-38, J-45 and J-69;
each Q independently represents Q-1, Q-20, Q-32 Q-34, inclusive, Q-45 Q-47, inclusive, Q-60 to Q-73, inclusive, Q-76-Q-79, inclusive, Q-84-Q-94 inclusive Q-101 or Q-102;
And represents CH2or NH;
W represents O;
each R5independently represents H, cyano, C1-C6alkyl, C1-C6halogenated,3-C8cycloalkyl,3-C8 halogenosilanes,2-C6alkoxyalkyl, C1-C6alkoxy, C1-C6halogenoalkane,3-C8cycloalkane,2-C6alkenylacyl,2-C6alkyloxy, C1-C6alkylthio, C1-C6allogenicity, -NR25R26or Z2Q;
Z1is a direct link;
Z2represents a direct bond or NR21;
R1selected from U-1 to U-3, inclusive, U-11, U-13, U-20, U-22, U-23, U-36 U-39 inclusive and U-50;
R3arepresents H;
R11arepresents H;
each R4aindependently represents a C1-C2alkyl, C1-C2halogenated, halogen, C1-C2alkoxy or1-C2halogenoalkane;
each R4bindependently represents a C1-C2alkyl;
each R7independently represents halogen, cyano, C1-C3alkyl, C1-C3halogenated, hydroxy, C1-C2alkoxy or C1-C2halogenoalkane;
k is 1 or 2; and
n is 0.

4. The compound according to claim 3, where
And represents CH2;
G is selected from G-1, G-2, G-15, G-26, G-27, G-36, G-37 and G-38;
J is selected from J-4, J-5, J-8, J-11, J-15, J-16, J-20, J-29, J-30, J-37, J-38 and J-69;
Q is selected from Q-1, Q-45, Q-63, Q-64, Q-65, Q-68, Q-69, Q-70, Q-71, Q-72, Q-73, Q-76, Q-78, Q-79, Q-84, Q-85, Q-101 and Q-102;
X is a X1or X2; and the ring is, containing X is saturated;
R1is a U-1 or U-50;
each R4aindependently represents a C1-C2alkyl, trifluoromethyl, CL, Br, I or methoxy;
and
each R5independently represents H, cyano, C1-C6alkyl, C1-C6halogenated, C1-C6alkoxy, C1-C6halogenoalkane, - NR25R26or Z2Q.

5. The compound according to claim 4 where
G is selected from G-1, G-2, G-15, G-26 and G-36;
J is selected from J-4, J-5, J-11, J-20, J-29, J-37, J-38 and J-69;
Q is selected from Q-45, Q-63, Q-64, Q-65, Q-68, Q-69, Q-70, Q-71, Q-72 and Q-85; and X is a X1.

6. The compound according to claim 5, where G is a G-1;
J represents a J-29;
each R5independently represents H or Z2Q;
Q is selected from Q-45, Q-63, Q-65, Q-70;
each R7independently represents a methyl, F, Cl, Br, hydroxy, cyano or methoxy;
Z2is a direct link;
p is 0, 1 or 2; and
x is an integer 1 or 2.

7. The compound according to claim 1, selected from the group consisting of:
4-[4-[(5R)-4,5-dihydro-5-phenyl-3-isoxazolyl]-2-thiazolyl]-1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]acetyl]piperidine and its enantiomer,
1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]acetyl]-4-[4-(5-phenyl-3-isoxazolyl)-2-thiazolyl]piperidine,
1-[4-[4-[(5R)-4,5-dihydro-5-methyl-5-phenyl-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-p is razol-1-yl]ethanone and its enantiomer,
2-[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]-1-[4-[4-[(3S,9bR),3A,4,5,9b-tetrahedronal[2,1-d]isoxazol-3-yl]-2-thiazolyl]-1-piperidinyl]ethanone and its enantiomer,
1-[4-[4-[(5R)-4,5-dihydro-5-phenyl-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-ethyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]ethanone and its enantiomer,
2-[3,5-bis(trifluoromethyl)-1H-pyrazole-1-yl]-1-[4-[4-[(5R)-4,5-dihydro-5-phenyl-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]ethanone and its enantiomer,
1-[4-[4-[(5R)-3',4'-dihydrospiro[isoxazol-5(4H),1',(2 N)-naphthalene]-3-yl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]ethanone and its enantiomer,
1-[4-[4-[(5R)-2,3-dihydrospiro[1H-inden-1,5'(4 N)-isoxazol]-3'-yl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]ethanone and its enantiomer,
2-[5-chloro-3-(trifluoromethyl)-3H-pyrazole-1-yl]-1-[4-[4-[(5R)-4,5-dihydro-5-phenyl-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]ethanone and its enantiomer,
2-[(5R)-4,5-dihydro-3-[2-[1-[2-[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]acetyl]-4-piperidinyl]-4-thiazolyl-5-isoxazolyl]-1H-isoindole-1,3(2H)-dione and its enantiomer,
2-[5-chloro-3-(trifluoromethyl)-1H-pyrazole-1-yl]-1-[4-[4-[(1R)-2,3-dihydrospiro[1H-inden-1,5'(4 N)-isoxazol]-3'-yl]-2-thiazolyl]-1-piperidinyl]ethanone and its enantiomer,
2-[5-chloro-3-(trifluoromethyl)-1H-pyrazole-1-yl]-1-[4-[4-[(1'R)-3',4'-dihydrospiro[isoxazol-5(4H),1'(2 N)-naphthalene]-3-yl]-2-thiazolyl]-1-piperidinyl]ethanone and its enantiomer,
2-[5-methyl-3-(trifluoromethyl)-1H-pee the azole-1-yl]-1-[4-[4-(3R)-Spiro[benzofuran-3(2H),5'(4 N)-isoxazol]-3'-yl-2-thiazolyl]-1-piperidinyl]ethanone and its enantiomer,
1-[4-[4-[(1R)-2,3-dihydrospiro[1H-inden-1,5'(4 N)-isoxazol]-3'-yl]-2-thiazolyl]-1-piperidinyl-2-(3,5-dimethyl-1H-pyrazole-1-yl)ethanone and its enantiomer,
2-[3,5-bis(trifluoromethyl)-1H-pyrazole-1-yl]-1-[4-[4-[(1R)-3',4'-dihydrospiro[isoxazol-5(4H), 1'(2 N)-naphthalene]-3-yl]-2-thiazolyl]-1-piperidinyl]ethanone and its enantiomer,
2-[3,5-bis(trifluoromethyl)-1H-pyrazole-1-yl]-1-[4-[4-[(1R)-2,3-dihydrospiro[1H-inden-1,5'(4 N)-isoxazol]-3'-yl]-2-thiazolyl]-1-piperidinyl]ethanone and its enantiomer,
1-[4-[4-[(5R)-5-(2,6-dichlorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]ethanone and its enantiomer,
1-[4-[4-[(5R)-4,5-dihydro-5-(2-forfinal)-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-H-pyrazole-1-yl]ethanone and its enantiomer,
1-[4-[4-[(5R)-4,5-dihydro-5-(2-were)-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]ethanone and its enantiomer,
1-[4-[4-[(5R)-5-(2,6-dimetilfenil)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]ethanone and its enantiomer,
1-[4-[4-[(5R)-4,5-dihydro-5-(2,4,6-trimetilfenil)-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]ethanone and its enantiomer,
1-[4-[4-[(1'R)-3',4'-dihydrospiro[isoxazol-5(4H), 1'(2 N)-naphthalene]-3-yl]-2-thiazolyl]-1-piperidinyl]-2-(3,5-dimethyl-1H-pyrazole-1-yl)ethanone and its enantiomer,
1-[4-[4-[(5R)-4,5-dihydro-5-(2,4,6-trimeton fenil)-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]ethanone and its enantiomer,
3-[(5R)-4,5-dihydro-3-[2-[1-[2-[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]acetyl]-4-piperidinyl]-4-thiazolyl]-5-isoxazolyl]-2(3H)-benzoxazolone and its enantiomer,
1-[4-[4-[(5R)-5-(2,6-differenl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]ethanone and its enantiomer,
2-[(5R)-4,5-dihydro-3-[2-[1-[2-[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]acetyl]-4-piperidinyl]-4-thiazolyl]-5-isoxazolyl]benzonitrile and its enantiomer,
2-[5-chloro-3-(trifluoromethyl)-1H-pyrazole-1-yl]-1-[4-[4-[(5R)-4,5-dihydro-5-methyl-5-phenyl-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]ethanone and its enantiomer,
2-[3,5-bis(trifluoromethyl)-1H-pyrazole-1-yl]-1-[4-[4-[(5R)-4,5-dihydro-5-methyl-5-phenyl-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]ethanone and its enantiomer,
1-[4-[4-[(5R)-5-(2-chlorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]ethanone and its enantiomer,
1-[4-[4-[(5R)-4,5-dihydro-5-phenyl-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[3-methyl-5-(trifluoromethyl)-1H-pyrazole-1-yl]ethanone and its enantiomer,
1-[4-[4-[(4S)-2,3-dihydrospiro[4H-1-benzopyran-4,5'(4 N)-isoxazol]-3'-yl)-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]ethanone and its enantiomer and
(5R)-4,5-dihydro-3-[2-[1-[2-[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]acetyl]-4-piperidinyl]-4-thiazolyl]-5-phenyl-5-isoxazolecarboxylic and its enantiomer.

8. A compound selected from formula V, and its salt

where each R4a1and R4a2independently represents a C1-C3alkyl, C1-C6halogenated, halogen, cyano, C1-C2alkoxy, C1-C2halogenoalkane, C1-C2alkylthio, C1-C2allogenicity or2-C3alkoxycarbonyl; and
Z3represents CN or C(=S)NH2.

9. The connection of claim 8, where
each R4a1and R4a2independently represents a C1-C3alkyl, C1-C3halogenated, halogen, cyano, C1-C3alkoxy or C1-C2halogenoalkane.

10. The compound of claim 8 selected from the group consisting of:
1-[2-[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]acetyl]-4-piperidinecarboxylate,
1-[2-[3,5-bis(trifluoromethyl)-1H-pyrazole-1-yl]acetyl]-4-piperidinecarboxylate,
1-[2-[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]acetyl]-4-piperidinecarbonitrile and
1-[2-[3,5-bis(trifluoromethyl)-1H-pyrazole-1-yl]acetyl]-4-piperidinecarbonitrile.

11. A compound selected from formula 1C, and its salt,

where M represents a C1-C3alkyl, C1-C3halogenated, hydroxy, C1-C4alkoxy, C1-C2halogenoalkane, C1-C4alkylamino,2-C8dialkylamino, 1-piperidinyl, 1-pyrrolidinyl or 4-morpholine is l; and
J1represents a

provided that the compound is not a
1-(4,5-dihydro-5-phenyl-3-isoxazolyl)Etalon.

12. A method of combating plant diseases caused by striking plant fungal pathogens of Oomycete class containing the application to the plant, or part thereof, or seed plants fungicide-effective amount of a compound selected from the group consisting of compounds according to claim 1, compounds with the exception of the conditions (a) according to claim 1, compounds with the exception of the conditions (b) according to claim 1, and compounds with the exception of the conditions (C) according to claim 1.

13. Fungicidal composition comprising (1) a compound selected from the group consisting of compounds according to claim 1, compounds, except condition (a) according to claim 1, connections, except the condition (b) according to claim 1, and compounds, except the condition (s) according to claim 1; and (2) at least one other fungicide.

14. Fungicidal composition comprising (1) fungicide-effective amount of a compound selected from the group consisting of compounds according to claim 1, compounds, except condition (a) according to claim 1, connections, except the condition (b) according to claim 1, and compounds, except the condition (s) according to claim 1; and (2) at least one additional component selected from the group consisting of surfactants, solid, R is zbawiciela and liquid diluents.



 

Same patents:

FIELD: chemistry.

SUBSTANCE: invention relates to novel substituted pyrimidine derivatives, having HIV replication inhibiting properties, or pharmaceutically acceptable salts thereof. In formula (1): R1 denotes hydrogen; R2 and R3 independently denote hydrogen; R7 and R8 denote C1-6alkyl; R4 denotes cyano; R9 denotes C1-6alkyl optionally substituted with cyano, C2-6alkenyl substituted with cyano, C2-6alkynyl optionally substituted with cyano; R5 denotes C1-6alkyl optionally substituted with Ar or Het; C2-6alkenyl optionally substituted with Ar or Het; C2-6alkynyl optionally substituted with Ar or Het; C3-7cycloalkyl; Ar; Het; R6 denotes H, Het; Y denotes -OR11, -NR12R13; R11 denotes hydrogen or C1-6alkyl optionally substituted with hydroxy, C1-6alkoxy or pyridyl; R12 denotes hydrogen or C1-6alkyl; R13 denotes hydrogen or C1-6alkyl; or R12 and R13 together with a nitrogen atom, which is substituted by said two substitutes, form a morpholinyl; imidazolyl; X denotes -NR1-; Het denotes 5- or 6-member completely saturated ring, where one or two ring members are heteroatoms, each independently selected from nitrogen and sulphur, and where the rest of the ring members are carbon atoms; and where any member of the heterocycle with a nitrogen heteroatom can optionally be substituted with C1-6alkyl; where the 5- or 6-member ring can optionally be annelated with a benzene or thiophene ring; each aryl independently denotes phenyl or phenyl substituted with one substitute selected from C1-6alkoxy.

EFFECT: high efficiency of using said compounds.

7 cl, 4 ex, 1 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to substituted heteroarylpiperidine derivatives of formula (I) and enantiomers, diastereomers, tautomers, solvates and pharmaceutically acceptable salts thereof, where R1 denotes -N(R10)-(C(R6)2)m-T, (C(R6)2)1-T or -O-(C(R6)2)m-T; R6 is independently selected from H, OCH3, C1-6-alkyl, possibly substituted with 1-3 substitutes which are halogen, and C3-6-cycloalkyl, possibly substituted with 1-3 substitutes which are halogen, T denotes NR7R8, , , , or ; R7 and R8 are independently selected from H, C1-6-alkyl; R9 is independently selected from OH, C1-6-alkyl, O-C1-6-alkyl, or NR12R13; R10 denotes H or C1-6-alkyl; R12 and R13 are independently selected from C1-6-alkyl, possibly substituted with OH, C2-6-alkylene-O-C1-6-alkyl and W denotes CH, O or NR10; B denotes CR2 or N; G denotes CR2 or N; D denotes CR2 or N; E denotes CR2 or N; provided that one or more of variables B, G, D and E must be N; R2 is independently selected from H, F, Cl, CH3, OCH3 and CF3; R3 denotes: H, CI, F or CH3; R4 denotes Cl, F or CH3, R5 denotes , morpholine, possibly substituted with 1-3 identical or different substitutes R14, a 4-7-member saturated or partially unsaturated heterocycle containing one nitrogen atom in the ring and possibly an additional heteroatom selected from O, N and S, where the heterocycle is possibly substituted with 1-4 identical or different substitutes R11, or NR12R13; R11 is indendently selected from halogen, OH, C1-6-alkyl, possibly substituted with 1-3 substitutes which are halogen, C2-6-alkynyl, -C0-6-alkyl-C3-6-cycloalkyl, -OC(O)C1-6-alkyl, -NH2, -NH(C1-6-alkyl) and -N(C1-6-alkyl)2; A denotes a 3-7-member saturated ring; R12 and R13 are independently selected from C1-6-alkyl, possibly substituted with OH, C2-6-alkylene-O-C1-6-alkyl; R14 denotes C1-6-alkyl; 1 equals 0, 1, 2, 3 or 4; m equals 0, 1, 2, 3 or 4; o equals 0, 1 or 2; p equals 0, 1, 2, 3 or 4; r equals 0, 1, 2, 3 or 4; s equals 1 or 2 and t equals 0 or 1. The invention also relates to use the compound of formula I to produce a drug for treating or preventing disorders, diseases or conditions responsible for inactivation or activation of the melanocortin-4 receptor in mammals, and to a pharmaceutical composition based on said compounds.

EFFECT: novel compounds which can be used as melanocortin-4 receptor modulators are obtained and described.

10 cl, 134 ex, 16 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of formula 1 or pharmaceutically acceptable derivatives thereof, where values of radicals X, W, R4, Ar1, Ar2, R3, R4, R20 are as described in paragraph 1 of the claim. The invention also describes a composition for treating or preventing pain, UI, ulcers, inflammatory bowel disease or irritable bowel syndrome.

EFFECT: compound which can be used in medicine is obtained and described.

46 cl, 10 ex, 1 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to novel compounds of formula (I)

, where: n equals 0, 1, 2; G denotes CH2, CHR3; R1 denotes H, C1-C6-alkyl, C3-C6-alkenyl, -CH2Ph; R2, R3, R4 independently denote H, CH3, -CH2F, -CHF2, CF3; A denotes 1,4-Ph, 1,3-Ph, which can be optionally substituted with 1-4 substitutes selected from halogen, C1-C4-alkyl, C1-C4alkoxy, fluorinated C1-C4-alkyl and fluorinated C1-C4alkoxy; E denotes NR5, where R5 denotes H, C1-C3-alkyl; Ar denotes a radical of formula

and

where: Ra denotes halogen, C1-C6-alkyl, fluorinated C1-C6-alkyl, C1-C6-alkoxy, fluorinated C1-C6-alkoxy, phenyl sulphonyl, CN, -NR6R7, where R6 and R7, together with an N atom, form a 5- or 6-member saturated ring or denotes a 5-member saturated or unsaturated aromatic or non-aromatic heterocyclic ring containing, as ring members, 1, 2 or 3 heteroatoms selected from N, O and S, and where the heterocyclic ring can carry 1, 2 or 3 substitutes selected from halogen and C1-C6-alkyl, or denotes a 6-member saturated heterocyclic ring containing, as ring members, one N and one O atom; Rb and Rc independently denote H, halogen, CH3, OCH3, CH2F, OCH2F, CHF2, OCHF2, CF3, OCF3, CH2CH2F, OCH2CH2F, CH2CHF2, OCH2CHF2, CH2CF3 or OCH2CF3; Rd denotes Ra or a 5- or 6-member heteroaromatic ring containing, as ring members, 1, 2 or 3 heteroatoms selected from N, O and S, and where the heteroaromatic ring can carry 1 substitute selected from C1-C6-alkyl and C1-C6-alkylthio; Re denotes H or is defined as Ra; Rf is defined as Ra; k equals 0, 1, 2, 3; j equals 0, 1, 2, 3, 4; provided that Ra does not denote F, CH2F, CHF2, CF3, OCF3, if A denotes 1,4-Ph, Ar denotes a radical of formula (A) and Rb and Rc denote H, halogen; except compounds, where R1 denotes propyl, G denotes CH2, n equals 1, A denotes 1,4- Ph, E denotes NH, Ar denotes a radical of formula (F) and Rd denotes halogen, C1-C6-alkyl, C2-C6-alkenyl or a 5-member heteroaromatic ring; and physiologically acceptable acid addition salts thereof.

EFFECT: compounds exhibit 5HT6 receptor simulating activity, which allows for their use in a pharmaceutical composition.

25 cl, 6 tbl, 107 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to compounds of general formula (I) X represents NH, n means a number equal to 0-3, Y represents a direct bond, -(CH2)pO-, -(CH2)q- or -(CH2)qSO2-, p means a number equal to 0-2, q means a number equal to 1-3, R1 represents hydrogen, -(CR4R5)P-A-R6 or -(CR4R5)q-R6, R2 represents halogen, C1-C3-alkyl or trifluoromethyl, or represents 5~6-member heteroaryl or heterocyclyl each of which has 1 -3 heteroatoms selected from N and O, or represents optionally substituted C1-C3-alkylsulphonyl 6~12-member aryl, R3 represents R7-X-B-X'-, B represents a direct bond or represents 5~6-member heterocyclyl or heteroaryl each of which optionally contains oxo, optionally condensed and has 1-4 heteroatoms selected from N, O and S. Also the invention refers to a pharmaceutical composition for glucokinase activation and a method for preparing it.

EFFECT: use of the compounds of formula (I) as glucokinase activators.

22 cl, 11 dwg, 3 tbl, 222 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a novel heteroaryl-substituted derivative of benzothiazole - 2-[6-(methylamino)pyridin-3-yl]-1,3-benzothiazol-6-ol where one or more atoms may be a detectable isotope, in form of a free base or pharmaceutically acceptable salt thereof, capable of binding with amyloid deposits, to pharmaceutical compositions based on the radioactive-labelled disclosed compound, to use of the detectable isotope-labelled disclosed compound for determining amyloid deposits, as well as use of the disclosed compound in producing a medicinal agent for preventing and/or treating Alzheimer's disease and familial Alzheimer's disease. The present invention also relates to a novel intermediate compound for producing the disclosed heteroaryl-substituted benzothiazole derivative

EFFECT: high efficiency of using the compounds during treatment.

15 cl, 1 tbl, 15 dwg, 82 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: present invention refers to a compound of formula

wherein R1, R2 and X are those as specified in cl.1 of the patent claim, or its pharmaceutically acceptable salt, as well as using such compound or its pharmaceutically acceptable salt for preparing a drug preparation for prevention and treatment of all types of sleeping, eating or drinking disorders.

EFFECT: preparing the new azetidine compounds showing activity of orexin receptor antagonists.

12 cl, 112 ex, 1 tbl

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to 2-piperidino-5-(thienyl-2)-6H-1,3,4-thiadiazines, hydrobromides (of general formula I) and 2-piperidino-5-(thienyl-3)-6H-1,3,4-thiadiazines, hydrobromides (of general formula II) which possess antiaggregant action. wherein R=H; Cl; Br R1=H; Cl.

EFFECT: given compounds may be used for preparing cardiologic drugs and enable better treatment of various cardiovascular diseases, including myocardial infarction and thrombotic apoplexy.

1 cl, 2 tbl, 5 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a novel purified compound PM 181104 of formula I

(with molecular weight 1514 and molecular formula C69H66N18O13S5), pharmaceutically acceptable salts thereof, methods for synthesis via fermentation of a microorganism of the type Kocuria (ZMA B-1 / MTCC 5269), as well as pharmaceutical compositions.

EFFECT: high efficiency of using the composition to produce a medicinal agent for treating bacterial infections.

20 cl, 4 dwg, 4 tbl, 16 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a compound of formula

or tautomer thereof

or enantiomer or physiologically acceptable salt, where R1 is o-bromo, R2 is n-fluoro, R3 is C1-C4 alkyl, R6 is thiazolyl-2-yl, X is methylene and Z is morpholinyl. The invention also relates to methods of producing (versions) compounds of formula (I) and (Ia). The compound of formula (I) or (Ia) is used to prepare a pharmaceutical composition for treating or preventing HBV infections and HBV-induced diseases such as hepatitis B.

EFFECT: bromophenyl substituted thiazolyl dihydropyrimidines for HBV infection control.

20 cl, 7 tbl, 14 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to compounds of general formula (I) X represents NH, n means a number equal to 0-3, Y represents a direct bond, -(CH2)pO-, -(CH2)q- or -(CH2)qSO2-, p means a number equal to 0-2, q means a number equal to 1-3, R1 represents hydrogen, -(CR4R5)P-A-R6 or -(CR4R5)q-R6, R2 represents halogen, C1-C3-alkyl or trifluoromethyl, or represents 5~6-member heteroaryl or heterocyclyl each of which has 1 -3 heteroatoms selected from N and O, or represents optionally substituted C1-C3-alkylsulphonyl 6~12-member aryl, R3 represents R7-X-B-X'-, B represents a direct bond or represents 5~6-member heterocyclyl or heteroaryl each of which optionally contains oxo, optionally condensed and has 1-4 heteroatoms selected from N, O and S. Also the invention refers to a pharmaceutical composition for glucokinase activation and a method for preparing it.

EFFECT: use of the compounds of formula (I) as glucokinase activators.

22 cl, 11 dwg, 3 tbl, 222 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing 3,3'-bi-1,5,3-dithiazepinane of formula (1) having fungicidal activity against Bipolaris sorokiniana, Aspergillus fumigates, Aspergillus niger and Paecilomyces variotii. The method involves reaction of a mixture of ethanedithiol and formaldehyde with hydrazine hydrate (60%) with molar ratio aldehyde: ethanedithiol: hydrazine = 40:20:10 at temperature 25°C and atmospheric pressure for 2-4 hours.

EFFECT: improved method.

2 cl, 2 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a novel heteroaryl-substituted derivative of benzothiazole - 2-[6-(methylamino)pyridin-3-yl]-1,3-benzothiazol-6-ol where one or more atoms may be a detectable isotope, in form of a free base or pharmaceutically acceptable salt thereof, capable of binding with amyloid deposits, to pharmaceutical compositions based on the radioactive-labelled disclosed compound, to use of the detectable isotope-labelled disclosed compound for determining amyloid deposits, as well as use of the disclosed compound in producing a medicinal agent for preventing and/or treating Alzheimer's disease and familial Alzheimer's disease. The present invention also relates to a novel intermediate compound for producing the disclosed heteroaryl-substituted benzothiazole derivative

EFFECT: high efficiency of using the compounds during treatment.

15 cl, 1 tbl, 15 dwg, 82 ex

FIELD: chemistry.

SUBSTANCE: invention relates to derivatives of 1,3,4-thiadiazolines (I), thiadiazinones (II) and thiadiazepines (III), obtained based on thiohydrazides of oxamic acids, which can be used to inhibit pathogenic bacteria, and can particularly affect type III secretion system in pathogens, having general formula:

, , ,

where R denotes H; R1 denotes H, pyridinyl; phenyl, substituted with alkyl C1-C5, Hal, CF3; a group , where X denotes S, substituted with alkyl C1-C5, COOR4; R2, R3 denotes alkyl C1-C5, pyridinyl, phenyl, substituted Hal, OH, OR4, a R4 denotes unsubstituted alkyl C1-C4.

EFFECT: obtaining compounds which can be used to inhibit pathogenic bacteria.

2 cl, 2 dwg, 6 tbl, 21 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a compound of formula

,

where R denotes a substituted or unsubstituted thiazolyl group of formula or ; R4 and R5, each independently, are selected from i) hydrogen; ii) a substituted or unsubstituted C1-C6 linear, C3-C6 branched or C3-C6 cyclic alkyl; iii) a substituted or unsubstituted phenyl; iv) a substituted or unsubstituted heteroaryl containing 5 or 6 ring atoms and 1 or 2 heteratoms, where the heteroatoms are selected from nitrogen, oxygen, sulphur and combination thereof; or R4 and R5 can be taken together to form a saturated or unsaturated ring, having 5-7 atoms; said substitutes are independently selected from one or more groups, selected from C1-C6 linear, C3-C6 branched or C3-C6 cyclic alkyl, halogen, hydroxyl or cyano; R6 denotes a group selected from i) hydrogen; ii) a substituted or unsubstituted C1-C6 linear, C3-C6 branched or C3-C6 cyclic alkyl; iii) a substituted or unsubstituted phenyl or iv) a substituted or unsubstituted heteroaryl containing 5 or 6 ring atoms and 1 or 2 heteroatoms, where the heteroatoms are selected from nitrogen, oxygen, sulphur and combination thereof; where said substitutes are independently selected from one or more groups selected from C1-C6 linear, C3-C6 branched or C3-C6 cyclic alkyl, halogen, hydroxyl or cyano; R1 is selected from i) hydrogen; ii) C1-C6 linear or C3-C6 branched alkyl; iii) a substituted or unsubstituted phenyl or iv) a substituted or unsubstituted benzyl; where said substitutes are independently selected from one or more groups selected from C1-C6 linear, C3-C6 branched or C3-C6 cyclic alkyl, halogen, hydroxyl or cyano; R2 is selected from i) C1-C6 linear or C3-C6 branched alkyl or ii) C1-C6 linear or C3-C6 branched alkoxy; R3 denotes hydrogen or C1-C4 linear or C3-C6 branched alkyl.

EFFECT: compounds of formula (I) are effective as human protein tyrosine phosphatase beta (HPTP-β) inhibitors.

20 cl, 10 tbl, 8 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: present inventions refers to a new crystalline form of tetomilast hydrate of the X-ray powder diffraction spectrum having characteristic peaks at the angle 20=10.6°, 12.9°, 21.1°, 22.3° and 25.0°, to a new crystalline form of anhydrous tetomilast type C of the X-ray powder diffraction spectrum having characteristic peaks at the angle 2θ=4.2°, 8.2°, 12.0°, 16.4°, 24.7° and 25.9°, to a new crystalline form of acetonitrile tetomilast solvate of the X-ray powder diffraction spectrum having characteristic peaks at the angle 2θ=3.6°, 7.1°, 10.6°, 14.2° and 24.8°, to based pharmaceutical compositions and to methods for preparing.

EFFECT: new crystalline forms shows useful processing characteristics with relation to preparing pharmaceutical drugs of them.

13 cl, 14 dwg, 8 ex

FIELD: chemistry.

SUBSTANCE: invention relates to indole and indazole compounds of formula in which n equals a whole number from 1 to 3, m equals 0 or 1, A denotes phenyl, X denotes C or N, R1 denotes hydrogen, alkyl, -(CH2)rNR7R8, where r equals a whole number from 1 to 5, and R7 and R8 independently denote hydrogen, alkyl or alkylcarbonyl, or can together form an optionally alkyl-substituted alkylene chain, where optionally one methylene is substituted with a N atom, R2 denotes hydrogen, halogen, cyano, nitro, hydroxy, alkyl, alkoxy or trialkylsilyl, denotes -(CH2)pCO2R7, -(CH2)pOR7, -(CH2)pNR7R8, -NHR10, -N(H)S(O)2R7, -NHC(O)R10, -(CH2)pS(O)2R7 or (CH2)p-heterocycle-R10, where p equals a whole number from 0 to 3, R7 and R8 are as defined above, R10 denotes hydrogen, oxo, alkylsulphonyl, alkylcarbonyl, alkyloxycarbonyl, alkoxy, alkyl or heterocycle, R3 denotes hydrogen, cyano, halogen, alkyl or phenyl, or denoes -(CH2)n-heterocycle or -(CH2)n-aryl, where n equals a whole number from 0 to 3, provided that R3 denotes phenyl when X denotes C and m=0, R4 denotes -YR11, where Y denotes a direct bond or -(CR7R8)pY′-, where p equals a whole number from 0 to 3, R7 and R8 are as defined above, Y′ is selected from a group consisting of -O-, -S-, -NR12-, -NR12C(O)-, -C(O)-, -C(O)O-, -C(O)NR12-, -S(O)q- and -S(O)qNR12-, where R12 denotes hydrogen, alkyl, aryl or heteroaryl, q equals a whole number from 0 to 2, R11 is selected from a group consisting of hydrogen, cyano, halogen, hydroxy, thiol, carboxy, alkyl and -(CH2)tB-R13, where t equals a whole number from 0 to 3, B denotes heterocycle, heteroaryl or aryl, R13 denotes hydrogen, cyano, halogen, hydroxy, oxo, thiol, carboxy, carboxyalkyl, alkylcarbonyloxy, alkyl, alkoxy, alkylthio, alkylcarbonyl or alkylsulphonyl, R5 denotes hydrogen, alkyl, cycloalkyl, heterocycle or heterocyclylalkyl, R6 denotes (CR7R8)p-Z-D-W-R14, where Z denotes a direct bond, or is selected from a group consisting of -C(O)-, -C(O)O, -C(O)NR12- and -S(O)y-, y equals a whole number from 1 or 2, D denotes a direct bond, or denotes cycloalkyl, heteroaryl or heterocycle, W denotes a direct bond, or denotes -NR -, -C(O)-, -C(O)O-, -C(O)NR12-, -S(O)y-, -S(O)yNR12- or -NR12S(O)y, wherein R14 denotes hydrogen, hydroxy, alkyl, alkoxy, heterocycle, heteroaryl, aryl or aralkyl, R5 and R6 together denote an alkylene chain, provided that R6 denotes cycloalkyl or heterocyclyl when X denotes N, where the heteroaryl is a 5-6-member aromatic ring containing 1-2 heteroatoms selected from N, O and S, the heterocycle is a 3-8-member ring containing 1-3 heteroatoms selected from N, O and S, where the alkyl, alkoxy, aryl, cycloalky, heterocycle and heteroaryl can be optionally substituted, and the substitutes, one or more, are selected from a group consisting of hydroxy, halogen, nitrile, amino, alkylamino, dialkylamino, carboxy, alkyl, alkoxy, carboxyalkyl, alkylcarbonyloxy, alkylthio, alkyloxycarbonyl, alkylaminocarbonyl, arylalkoxy and oxo, and pharmaceutically acceptable salts or stereoisomers thereof. The invention also relates to a composition, as well as a method of preparing said composition.

EFFECT: obtaining novel biologically active compounds for preventing or treating necrosis and necrosis-associated diseases.

40 cl, 162 ex, 2 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of general formula where R denotes a thiazolyl group of formula R2 and R3 are selected from: hydrogen, C1-C3linear alkyl; R4 is selected from: C1-C3linear or C3cyclic alkyl, phenyl and thiophenyl; Z denotes a group of formula: -(L)n-R1; R1 is selected from: i) C1-C3linear or branched alkyl, optionally substituted with C1-C4alkoxycarbonyl, halogen; ii) substituted phenyl or substituted with one or two substitutes selected from halogen, methoxy- or hydroxy group, C1-C4alkoxycarbonyl; iii) dioxopiperazinyl and 2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl, substituted with C1-C3alkyl; or iv) heteroaryl rings containing 5-10 atoms selected from thiazole, triazole, 1H-imidazole, thiadiazole, oxazole, isoxazole, oxadiazole, benzodioxole, benzo(1,4)dioxepanyl, pyridine, pyrimidine, 1H-indole, 2,3-dihydrobenzo[b][1,4]dioxynil, which can be substituted with oine or two substitutes selected from: a) hydroxy; b) C1-C3alkyl (which can be substituted with one more two substitutes selected from: ) phenyl; ii) C1-C4alkoxycarbonyl; iii) naphthalenyl; iv) 2-methylthiazolyl) ; c) NHC(O)C1-C3alkyl; d) C1-C4alkoxycarbonyl; e) 1 -(tert-butoxycarbonyl)-2-phenylethyl; f) methoxybenzyl; g) phenyl which can be substuted with C1-C4alkoxy, halogen, methoxycarbonyl or >NHC(O)CH3; h) (methoxy-2-oxoethyl)carbamoyl; L denotes a group selected from: i) C(O)NH[C(R5aR5b)]w-; ii) -C(O)[C(R6aR6b)]x-; iii) -C(O)[C(R7aR7b)]yC(O)-; iv) -SO2[C(R8aR8b)]z-; R5a, R5b, R6a, R6b, R7a, R7b, R8a and R8b, each independently denotes: i) hydrogen; ii) C1-C3 linear alkyl which can be substituted with 1 or 2 halogen atoms; iii) phenyl which can be substituted with 1-2 substitutes selected from halogen and lower alkoxy; iv) heteroaryl rings selected from imidazolyl, imidazolyl substituted with methyl, benzo(1,4)oxazinyl, oxadiazolyl substituted with methyl; index n equals 0 or 1; indices w, x, y and z are each independently equal to a number from 1 to 3. The invention also relates to pharmaceutically acceptable salts of compounds of formula (I) and use of compounds of formula (I) to prepare a medicinal agent for treating protein tyrosine phosphatase beta-mediated conditions.

EFFECT: obtaining compounds of formula (I) as human protein tyrosine phosphatase beta (HPTP-β) inhibitors.

15 cl, 17 dwg, 13 tbl, 16 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention relates to derivatives of 5-amino-3-(2-nitroxipropyl)-1,2,4-thiadiazoles of general formula , where R1, R2 can be similar or different and independently represent hydrogen, substituted or non-substituted aryl or heteroaryl or aralkyl, alkyl, cycloalkyl, and R1 + R2 can represent heteroaryl (optionally substituted piperasin and piperidin).

EFFECT: obtained are novel compounds, which can be applied in medicine for treatment of neurodegenerative diseases.

1 cl, 3 ex

FIELD: chemistry.

SUBSTANCE: invention relates to novel carbostyril compounds of general formula (1) or salts thereof with common pharmaceutically acceptable acids or pharmaceutically acceptable basic compounds, having activity on promotion of TFF2 production, a pharmaceutical composition based on said compounds, an agent based on disclosed compounds used in case of a disorder where up-regulation of TFF has a prophylactic and/or therapeutic effect, use of disclosed compounds to prepare said agent and a method of producing disclosed compounds. The invention also relates to novel specific carbostyril compounds or salts thereof with common pharmaceutically acceptable acids or pharmaceutically acceptable basic compounds. In structural formula (1), A is a direct bond, a lower alkylene group or lower alkylidene group, X is an oxygen or sulphur atom, the bond between positions 3 and 4 of the carbostyril backbone is a single bond or a double bond, R4 and R5 each denotes a hydrogen atom provided that, when the bond between positions 3 and 4 of the carbostyril backbone is a double bond, R4 and R5 can instead be bonded to each other in form of a -CH=CH-CH=CH- group, and R1, R2 and R3 assume values given in the claims.

EFFECT: high efficiency of compositions based on said compounds.

32 cl, 23 dwg, 184 tbl, 1535 ex

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of general formula (I),

, where groups and radicals R1, R2 independently denote H, C1-8-alkyl or C3-7-cycloalkyl, where the alkyl or cycloalkyl group can be mono- or poly-substituted with identical or different groups R11; or R2 denotes a -CH2- or -CH2-CH2- bridge which is bonded with a group Y, and R1 is as defined above, or denotes a group selected from C1-4-alkyl-CO-, C1-4-alkyl-O-CO-, (C1-4-alkyl)NH-CO- or (C1-4-alkyl)2N-CO-, where the alkyl groups can be mono- or polyfluorinated; or R1 and R2 form an alkylene bridge such that R1R2N- denotes a group selected from: azetidine, pyrrolidine, piperdine, azepan, 2,5-dihydro-1H-pyrrole, 1,2,3,6-tetrahydropyridine, 2,3,4,7-tetrahydro-1H-azepine, 2,3,6,7-tetrahydro-1H-azepine, piperazine, in which the free amino group is substituted with R13, piperidin-4-one, morpholine, thiomorpholine, 4-C1-4-alkoxy iminopiperidin-1-yl and 4-hydroxy iminopiperidin-1-yl. Wherein, when R1 and R2 form an alkylene bridge, one or more H atoms in the alkylene bridge can be substituted with identical or different groups R14, and X denotes a C1-3-alkylene bridge which can contain one, two or three identical or different C1-3-alkyl substitutes; and Y denotes a group of subformula selected from: and , where the group can be mono-substituted with a substitute R20; Z denotes -CH2-CH2- or -C(=O)-CH2-; U, V both denote CH, one of groups U, V denotes N, and the other of U, V denotes CH, where CH can be substituted with L; and L independently denotes halogen, cyano or C1-3-alkyl; and k equals 0, 1 or 2; W is selected from a group consisting of -CH2-O- and -O-CH2-; B is selected from a group consisting of phenyl, pyridyl, pyridazinyl, pyrazinyl, pyrimidinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, furyl, thiophenyl and thiazolyl; each of which can be mono- or poly-substituted with identical or different substitutes R20; radicals R11, R13, R14, R20 assume values given in claim 1. The invention also relates to a pharmaceutical composition containing at least one compound of formula I and having action on MCH receptor.

EFFECT: disclosed pharmaceutical compositions are useful in treating metabolic disorders or eating disorders, especially obesity, bulimia, anorexia, hyperphagia and diabetes.

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