C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 487/18 (2006.01) A61K 31/437 (2006.01) A61P 31/04 (2006.01)
Patent
CA 2739776
The invention relates to nitrogenous heterocyclic compounds of the formula (I) where: R1 is hydrogen, -(CH2)m-NH2, -(CH2)m-NH(C1-C6)alc, -(CH2)m-N(C1-C6)alc2, - (CH2)m-NH-C(NH)NH2 or -(CH2)m-NH-CH=NH, m being equal to 1 or 2; R2 and R3 together form an aromatic nitrogenous heterocycle with 5 vertexes including 1, 2 or 3 nitrogen atoms, substituted by R4 on a nitrogen atom; R4 is hydrogen, (C1-C6)alc or a chain of the formula -(A)n-(NH)0-(CH2)p-(CHR')q R"; A is C=O, C=NH or SO2; R' is hydrogen or carboxy; R" is hydrogen, NH2, NH(C1-C6)alc, N(C1-C6)aIc2, CONH2, CONH(C1 -C6)alc, CON(C1-C6)alc2, or a saturated heterocycle with 5 or 6 vertexes including 1 or 2 nitrogen atoms and optionally an oxygen or sulphur atom bonded to the chain by a nitrogen or carbon atom and optionally substituted by (C1-C6)alc; n, o and q are 0 or 1 and p is an integer from 0 to 4; R5 is OSO3H, OCFCO2H or OCF2CO2H; R1 being different from hydrogen, -(CH2)m-NH2, -(CH2)m-NH(C1-C6)alc or -(CH2)m-N(C1- C6)alc2 when R4 is hydrogen, -(C1-C6)alc, -(C=O)n-(CH2)(0-5-NH2, -(C=O)n-(CH2)(0-5)- NH(C1-C6)alc or -(C=0)n-(CH2)(o-5-N(C1-C6)alc2 and R5 is a OSO3H group, or when R4 has all the values of the above R" except for heterocycle; and n, o, p and q cannot all be O except when R" is hydrogen or CONH2, CONH(C1- C6)alc, CON(C1-C6)alc2 or heterocycle; the invention relates to these compounds in the free form thereof or in zwitterion form or in the form of salts with pharmaceutically acceptable mineral or organic bases and acids, to the preparation thereof, and to the use thereof as antibacterial drugs.
The invention relates to nitrogenous heterocyclic compounds of the formula (I) where: R1 is hydrogen, -(CH2)m- NH2, -(CH2)m-NH(C1-C6)alc, -(CH2)m N(C1-C6)alc2, -(CH2)m-NH-C(NH)NH2 or - (CH2)m-NH-CH=NH, m being equal to 1 or 2; R2 and R3 together form an aromatic nitrogenous heterocycle with 5 vertexes including 1, 2 or 3 nitrogen atoms, substituted by R4 on a nitrogen atom; R4 is hydrogen, (C1-C6)alc or a chain of the formula -(A)n- (NH)0-(CH2)p-(CHR')qR"; A is C=O, C=NH or SO2; R' is hydrogen or carboxy; R" is hydrogen, NH2, NH(C1-C6)alc, N(C1-C6)aIc2, CONH2, CONH(C1-C6)alc, CON(C1-C6)alc2, or a saturated heterocycle with 5 or 6 vertexes including 1 or 2 nitrogen atoms and optionally an oxygen or sulphur atom bonded to the chain by a nitrogen or carbon atom and optionally substituted by (C1-C6)alc; n, o and q are 0 or 1 and p is an integer from 0 to 4; R5 is OSO3H, OCFCO2H or OCF2CO2H; R1 being different from hydrogen, -(CH2)m- NH2, -(CH2)m-NH(C1-C6)alc or -(CH2)m- N(C1-C6)alc2 when R4 is hydrogen, -(C1-C6)alc, -(C=O)n-(CH2)(0-5-NH2, -(C=O)n- (CH2)(0-5)- NH(C1-C6)alc or -(C=0)n-(CH2)(0-5- N(C1-C6)alc2 and R5 is a OSO3H group, or when R4 has all the values of the above R" except L'invention concerne des composés hétérocycliques azotés de formule (I) dans laquelle : R1 représente hydrogène, - (CH2)m-NH2, -(CH2)m-NH(C1-C6)alc, -(CH2)m-N(C1-C6)alc2, - (CH2)m-NH-C(NH)NH2 ou -(CH2)m-NH-CH=NH, m est égal à 1 ou 2; R2 et R3 forment ensemble un hétérocycle azoté à caractère aromatique à 5 sommets renfermant 1, 2 ou 3 atomes d'azote, substitué sur un atome d'azote par R4; R4 représente hydrogène, (C1-C6)alc ou une chaîne de formule :-(A)n (NH)0-(CH2)p- (CHR')q R"; A représente C=O, C=NH ou SO2; R' représente hydrogène ou carboxy; R" représente hydrogène, NH2, NH(C1- C6)alc, N(C1-C6)aIc2, CONH2, CONH(C1-C6)alc, CON(C1-C6)alc2, ou un hétérocycle saturé à 5 ou 6 sommets renfermant 1 ou 2 azotes et le cas échéant un oxygène ou un soufre, fixé à la chaîne par un azote ou par un carbone et éventuellement substitué par (C1-C6)alc; n, o et q représentent 0 ou 1 et p représente un entier de 0 à 4; R5 représente OSO3H, OCFCO2H ou OCF2CO2H; - R1, étant différent d'hydrogène, -(CH2)m-NH2, -(CH2)m-NH(C1-C6)alc ou -(CH2)m-N(C1- C6)alc2 lorsque R4 est hydrogène, -(C1-C6)alc, -(C=O)n-(CH2)(0-5-NH2, -(C=O)n-(CH2)(0-5)- NH(C1-C6)alc ou -(C=0)n-(CH2)(o-5- N(C1-C6)alc2 et R5 est un groupe OSO3H, ou lorsque R4 a l'ensemble des valeurs de R" ci-dessus à l'exception d' hétérocycle, - et n, o, p et q ne pouvant tous être O sauf lorsque R" est hydrogène ou CONH2, CONH(C1-C6)alc, CON(C1-C6)alc2 ou hétérocycle; sous forme libre et sous forme de zwitterions et de sels avec les bases et les acides minéraux ou organiques pharmaceutiquement acceptables, leur préparation et leur utilisation comme médicaments antibactériens.
Gourdel Marie-Edith
Kebsi Adel
Ledoussal Benoit
Pierres Camille
Renaud Emilie
Novexel
Robic
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