Derivatives of heterocycles with 5 members, their preparation and their use as medicaments

A method of treating Parkinson's disease in warm-blooded animals comprising administering to warm-blooded animals in need thereof an amount of a compound of the formula

• in racemic, enantiomeric form or any combination of these forms,
• in which
• A is
• in which Q is selected from the group consisting of H, —OR22, —NR23R24, phenyl optionally substituted by at least one substituent independently selected from the group consisting of zOH, cyano, nitro, alkyl, alkoxy or —NR10R11 and a group with two substituents representing together a methylenedioxy or ethylenedioxy, or Q is selected from the group consisting of —COPh, —SO2Ph or —CH2Ph, said COPh, —SO2Ph or —CH2Ph optionally substituted on its aromatic parts by at least one independently alkyl or alkoxy or halogen,
• R10 and R11 are independently selected from the group consisting of hydrogen, alkyl and —COR12, or R10 and R11 form together with the nitrogen atom an optionally substituted heterocycle containing 4 to 7 members and 1 to 3 heteroatoms including the nitrogen atom already present, the additional heteroatoms being independently selected from the group consisting of O, N and S,
• R12 is selected from the group consisting of hydrogen, alkyl, alkoxy and —NR13R14,
• R13 and R14 are independently hydrogen or alkyl, or R13 and R14 form together with the nitrogen atom an optionally substituted heterocycle containing 4 to 7 members and 1 to 3 heteroatoms including the nitrogen atom already present, the additional heteroatoms being chosen independently from the group consisting of O, N and S,
• R22 is selected from the group consisting of hydrogen, alkyl and aryl optionally substituted by at least one substituent selected from the group consisting of alkyl, —OH, halogen, nitro and alkoxy,
• R23 and R24 are independently selected from the group consisting of hydrogen, alkyl and —CO—R25,
• R25 is alkyl,
• and R19, R20 and R21 are independently selected from the group consisting of hydrogen, halogen, —OH, —SR26, alkyl, cycloalkyl, alkenyl, alkoxy, cyano, nitro, —SO2NHR49, —CONHR55, —S(O)qR56, —NH(CO)R57, —CF3, —OCF3 and —NR27R28,
• R27 and R28 are independently selected from the group consisting of hydrogen, alkyl and —COR29, or R27 and R28 form together with the nitrogen atom an optionally substituted heterocycle containing 4 to 7 members and 1 to 3 heteroatoms including the nitrogen atom already present, the additional heteroatoms being independently selected from the group consisting of O, N and S,
• R49 and R55 are independently each time that they occur, hydrogen or alkyl or alkylcarbonyl,
• q is an integer from 0 to 2,
• R56 and R57 are, each time that they occur, hydrogen or alkyl or alkoxy,
• R29 is selected from the group consisting of hydrogen, alkyl, alkoxy and —NR30R31,
• R30 and R31 are independently selected from the group consisting of hydrogen and alkyl, or R30 and R31 form together with the nitrogen atom an optionally substituted heterocycle containing 4 to 7 members and 1 to 3 heteroatoms including the nitrogen atom already present, the additional heteroatoms being independently selected from the group consisting of O, N and S,
• Y is O;
• R1 is hydrogen, alkyl, aminoalkyl, alkoxyalkyl, cycloalkyl, cycloalkylalkyl, trifluoromethyl, alkyl, alkenyl, allenyl, allenylalkyl, alkynyl, cyanoalkyl, —(CH2)g-Z1R39, —(CH2)g—COR40, —(CH2)g—NHCOR70, aryl, aralkyl, arylcarbonyl, heteroarylalkyl and aralkylcarbonyl, the aryl group of the aryl, aralkyl, arylcarbonyl, heteroarylalkyl or aralkylcarbonyl itself being optionally substituted by at least one substituent selected from the group consisting of alkyl halogen, alkoxy, nitro, cyano, cyanoalkyl, amino, alkylamino, dialkylamino, —(CH2)k-Z2R39 and —(CH2)k—COR40—,
• Z1 and Z2 are selected from the group consisting of a bond, —O—, —NR41— and —S—,
• R39 and R41 are independently each time that they occur, selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl and cyanoalkyl,
• R40 is, independently each time that it occurs, selected from the group consisting of hydrogen, alkyl, allenyl, allenylalkyl, alkenyl, alkynyl, cyanoalkyl, alkoxy and —NR42R43,
• R42 and R43 are independently, each time that they occur, selected from the group consisting of hydrogen, alkyl, allenyl, allenylalkyl, alkenyl, alkynyl and cyanoalkyl and R2 is selected from the group consisting of hydrogen, alkyl, aminoalkyl, alkoxyalkyl, cycloalkyl, cycloalkylalkyl, trifluoromethylalkyl,
• —(CH2)g—NHCOR71, aralkyl and heteroarylalkyl optionally substituted on the aryl or heteroaryl by at least one member selected from the group consisting of halogen, alkyl, alkoxy, hydroxyl, cyano, nitro, amino, alkylamino and dialkylamino,
• R70 and R71 are independently alkyl or alkoxy;
• or R1 and R2, taken together with the carbon atom which carries them, form a carbocycle with 3 to 7 members;
• B is selected from the group consisting of hydrogen, alkyl, —(CH2)g-Z3R44 and carbocyclic aryl optionally substituted 1 to 3 times by a member selected from the group consisting of halogen, alkyl and alkoxy of 1 to 6 carbon atoms, hydroxy, cyano, nitro, amino, alkylamino, dialkylamino and a carbocyclic aryl,
• Z3 is selected from the group consisting of a bond, —O—, NR45— and —S—,
• R44 and R45 are independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, allenyl, allenylalkyl and cyanoalkyl;
• Ω is —NR46R47;
• R46 and R47 are independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkynyl, allenyl, allenylalkyl, cyanoalkyl, —(CH2)g-Z4R50, —(CH2)k—COR51, —(CH2)k—COOR51, —(CH2)k—CONHR51, —SO2R51, aryl, aralkyl, aryloxyalkyl, arylcarbonyl, arylimino, aralkylcarbonyl, heteroaryl, pyridinylalkyl or pyridinylcarbonyl, the aryl or heteroaryl of said aryl, aralkyl, aryloxyalkyl, arylcarbonyl, arylimino, aralkylcarbonyl, heteroaryl, pyridinylalkyl or pyridinylcarbonyl being optionally substituted by at least one member independently selected from the group consisting of halogen, alkyl, alkoxy, hydroxy, nitro, cyano, cyanoalkyl, amino, alkylamino, dialkylamino, -Z5R50, —(CH2)k—COR51 and —(CH2)k—COOR51,
• Z4 and Z5 are selected from the group consisting of a bond, —O—, —NR52— and —S—, or R46 and R47 taken together form with the nitrogen atom a non-aromatic heterocycle with 4 to 8 ring members, the elements of the chain being selected from the group consisting of —CH(R53)—, —NR54—, —O—, —S— and —CO—,
• R50 and R52 are independently each time that they occur, selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, allenyl, allenylalkyl and cyanoalkyl,
• R51 is, independently each time that they occur, selected from the group consisting of hydrogen, cycloalkyl and cycloalkylalkyl in which the cycloalkyl has 3 to 7 carbon atoms, alkyl of 1 to 8 carbon atoms, alkenyl, alkynyl, allenyl, allenylalkyl, cyanoalkyl, alkoxyalkyl, —NR58R59, aryl or aralkyl, said aryl or aralkyl optionally substituted by at least one member selected from the group consisting of halogen, alkyl and alkoxy,
• R58 and R59 are independently a member selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, allenyl, allenylalkyl and cyanoalkyl,
• R53 and R54 are independently a member selected from the group consisting of hydrogen or —(CH2)k-Z7R60 and —(CH2)k—COR61,
• Z7 is a member selected from the group consisting of a bond, —O—, —NR62— and —S—,
• R60 and R62 are independently a member selected from the group consisting of hydrogen, alkyl, alkenyl, allenyl, allenylalkyl, alkynyl, cyanoalkyl, aryl, aralkyl, arylcarbonyl, aralkylcarbonyl, pyridinyl, pyridinylalkyl or pyridinylcarbonyl, the aryl or pyridinyl of the aryl, aralkyl, arylcarbonyl, aralkylcarbonyl, pyridinyl, pyridinylalkyl or pyridinylcarbonyl being optionally substituted by at least one substituent selected from the group consisting of alkyl, halogen, nitro, alkoxy, cyano, cyanoalkyl, —(CH2)k-Z8R63 and —(CH2)k—COR64,
• R61 is a member selected from the group consisting of hydrogen, alkyl, allenyl, allenylalkyl, alkenyl, alkynyl, cyanoalkyl, alkoxy and —NR65R66,
• R65 and R66 are independently selected from the group consisting of hydrogen, alkyl, allenyl, allenylalkyl, alkenyl, alkynyl and cyanoalkyl,
• Z8 is a member selected from the group consisting of a bond, —O—, —NR67— and —S—,
• R63 and R67 are independently a member selected from the group consisting of hydrogen, alkyl, allenyl, allenylalkyl, alkenyl, alkynyl and cyanoalkyl,
• R64 is a member of the group consisting of hydrogen, alkyl, allenylalkyl, alkenyl, alkynyl, cyanoalkyl, alkoxy and —NR68R69,
• R68 and R69 are independently a member selected from the group consisting of hydrogen, alkyl, allenyl, allenylalkyl, alkenyl, alkynyl cyanoalkyl,
• and R48 is a member selected from the group consisting of hydrogen, alkyl, alkynyl and cyanoalkyl;
• g and p, each time that they occur, being independently integers from 1 to 6, and k and n, each time that they occur, being independently integers from 0 to 6;
• or a salt thereof sufficient to treat Parkinson's disease.