Patent EP-0245170-B1 (EP)
IPC: C07J63/00
Filed: 1987-05-04
Granted: 1989-11-29
Abstract: 1. The products of formula I :   see diagramm : EP0245170,P90,F1   in which R1 represents an alkynyl radical having from 2 to 8 carbon atoms optionally substituted by a radical selected from the radicals, hydroxyl, halogen, trialkylsilyl, alkoxy, alkylthio, dialkylamino and oxo, R2 represents an alkyl radical having from 1 to 3 carbon atoms, the rings _A and _B have one of the following structures ; a/. either _A and _B represent the group :   see diagramm : EP0245170,P90,F2   in which R' and R" identical or different represent a hydrogen atom or an alkyl radical having from 1 to 4 carbon atoms ; b/. or _A and _B represent the group :   see diagramm : EP0245170,P90,F3   in which Rx represents a hydrogen atom or an ORe group in which Re represents a hydrogen atom, an alkyl radical containing from 1 to 6 carbon atoms optionally substituted by a dialkylamino radical or an acetyl or propionyl radical ; c/. or _A and _B represent the group :   see diagramm : EP0245170,P90,F4   d/. or _A and _B represent the group :   see diagramm : EP0245170,P90,F5   e/. or _A and _B represent the group :   see diagramm : EP0245170,P91,F1   in which R3 represents a hydrogen atom, an alkyl radical having from 1 to 8 carbon atoms or an aralkyl radical having from 7 to 15 carbon atoms ; - the group of formula :   see diagramm : EP0245170,P91,F2   represents : a/. either :   see diagramm : EP0245170,P91,F3   in which R3 and R4 , identical or different, represent either a hydrogen atom, a hydroxyl radical, an Oalk4 , or   see diagramm : EP0245170,P91,F4   radical, alk4 and alk5 representing an alkyl radical having from 1 to 8 carbon atoms or a benzyl radical ; an alkyl, alkenyl or alkynyl radical having at the most 8 carbon atoms or a phenyl, benzyl or phenylethyl or pyridylethynyl, thienyl or furyl radical, each of these radicals being optionally substituted by one or more radicals selected from the group formed by the radicals hydroxy, alkoxy and alkylthio having from 1 to 4 carbon atoms, the halogen atoms and the dialkylamino radical, or R3 and R4 together form the following radicals :   see diagramm : EP0245170,P91,F5     see diagramm : EP0245170,P91,F6     see diagramm : EP0245170,P91,F7     see diagramm : EP0245170,P91,F8     see diagramm : EP0245170,P91,F9     see diagramm : EP0245170,P91,F10     see diagramm : EP0245170,P91,F11     see diagramm : EP0245170,P91,F12     see diagramm : EP0245170,P91,F13     see diagramm : EP0245170,P91,F14     see diagramm : EP0245170,P91,F15     see diagramm : EP0245170,P91,F16     see diagramm : EP0245170,P91,F17     see diagramm : EP0245170,P91,F18   in which R5 and R6 together form a hydrogen atom or an alkyl radical having from 1 to 4 carbon atoms, M represents a hydrogen, sodium or potassium or lithium atom, R20 represents an alkyl radical optionally substituted by hydroxyl and R17 represents a hydrogen atom or an acetyl radical, Y and Z represent the following groups :   see diagramm : EP0245170,P92,F1     see diagramm : EP0245170,P92,F2     see diagramm : EP0245170,P92,F3     see diagramm : EP0245170,P92,F4     see diagramm : EP0245170,P92,F5   in which R7 and R8 represent an alkyl radical having from 1 to 4 carbon atoms ; b/. or :   see diagramm : EP0245170,P92,F6   in which R3 , R4 and Y-Z have the definitions previously indicated, the wavy lines meaning that the substituents R2 , R7 and R8 acan be found in one or other of the possible configurations, as well as the addition salts of the products of formula I with acids and bases.