RU2008102156A - NEW FURO- AND THIENO [2,3-b] -QINOLIN-2-CARBOXAMIDES, METHOD FOR OBTAINING AND ANTI-TUBERCULOSIS ACTIVITY - Google Patents

Abstract

1. Azaheterocyclic compounds, which are substituted furo [2,3-b] quinoline-2-carboxamides and substituted thieno [2,3-b] quinoline-2-carboxamides or their racemates, or their optical isomers, as well as their pharmaceutically acceptable salts and / or hydrates of the general formula (I)! ! where each of R1, R2, R3, R4 represents a substituent of the cyclic system selected from hydrogen, halogen, optionally substituted alkyl; a possibly substituted alkoxy group; optionally substituted cycloalkyl; optionally substituted aryl or heterocyclyl; ! X represents a heteroatom selected from oxygen or sulfur; ! R5 and R6 are independently amino substituents selected from hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heterocyclyl, ethoxycarbonyl, carboxamide, or R5 and R6 together with the nitrogen atom to which they are attached form optionally substituted azaheterocycle. ! 2. The compounds according to claim 1, which are substituted furo [2,3-b] quinoline-2-carboxamides and thieno [2,3-b] quinoline-2-carboxamides containing a piperidine, piperazine or pyrrolidine fragment of the general formula II :! ! ! where R1, R2, R3, R4 and X have the above meaning; W represents substituted piperidine, piperazine or pyrrolidine; ! R6, R7, R8, R9 and R10 are independently hydrogen, optionally substituted alkyl, cycloalkyl, aryl, heteroaryl, heterocyclyl, ethoxycarbonyl, heteroaroyl, carbamoyl; ! n is the number of substituted -C (R11R12) - groups; n takes values from 0 to 3; ! R11, R12 are substituted alkyl, cycloalkyl, aryl, heteroaryl, as well as hydrogen; ! U - represents

Claims (10)

1. Azaheterocyclic compounds, which are substituted furo [2,3-b] quinoline-2-carboxamides and substituted thieno [2,3-b] quinoline-2-carboxamides or their racemates, or their optical isomers, as well as their pharmaceutically acceptable salts and / or hydrates of the general formula (I)

where each of R ¹ , R ² , R ³ , R ⁴ represents a Deputy of the cyclic system selected from hydrogen, halogen, possibly substituted alkyl; a possibly substituted alkoxy group; optionally substituted cycloalkyl; optionally substituted aryl or heterocyclyl; X represents a heteroatom selected from oxygen or sulfur; R ⁵ and R ^{6 are} independently amino substituents selected from hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heterocyclyl, ethoxycarbonyl, carboxamide, or R ⁵ and R ⁶ together with a nitrogen atom with which they are connected, form an optionally substituted azaheterocycle. 2. The compounds according to claim 1, which are substituted furo [2,3-b] quinoline-2-carboxamides and thieno [2,3-b] quinoline-2-carboxamides containing a piperidine, piperazine or pyrrolidine fragment of the general formula II :

where R ¹ , R ² , R ³ , R ⁴ and X have the above meaning; W represents substituted piperidine, piperazine or pyrrolidine; R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ independently represent hydrogen, optionally substituted alkyl, cycloalkyl, aryl, heteroaryl, heterocyclyl, ethoxycarbonyl, heteroaroyl, carbamoyl; n is the number of substituted -C (R ¹¹ R ¹² ) - groups; n takes values from 0 to 3; R ¹¹ , R ¹² are substituted alkyl, cycloalkyl, aryl, heteroaryl, as well as hydrogen; Y - represents carbon or nitrogen. 3. The compounds according to claim 1 or 2, which are substituted N - ((piperidin-4-yl) methyl) furo [2,3-b] quinoline-2-carboxamides and substituted N - ((piperidin-4-yl) methyl) thieno [2,3-b] quinoline-2-carboxamides of the general formula III:

where R ¹ , R ² , R ¹⁰ and X have the above meaning. 4. The method of obtaining furo [2,3-b] quinoline-2-carboxamides (X = O) 3 and thieno [2,3-b] quinoline-2-carboxamides (X = S) 4 according to any one of claims 1- 3 by reacting substituted carboxylic acids 1 with suitable amines 2 in the presence of 1,1'-carbonyldiimidazole (CDI) in an organic solvent.

5. A drug substance for pharmaceutical compositions and finished dosage forms having anti-tuberculosis activity and representing compounds of general formula I, according to any one of claims 1 to 3. 6. A pharmaceutical composition having anti-tuberculosis activity, comprising a pharmaceutically effective amount of a drug substance according to claim 5. 7. The method of obtaining the pharmaceutical composition according to claim 6 by mixing an effective amount of a drug substance with an inert excipient and / or solvent, characterized in that the drug substance according to claim 5 is used as a drug substance. 8. A drug in the form of tablets, capsules or injections, placed in a pharmaceutically acceptable package, for the prevention and treatment of tuberculosis, comprising the drug substance according to claim 5 or the pharmaceutical composition according to claim 7. 9. Therapeutic cocktail for the prevention and treatment of tuberculosis in animals and humans, including the drug of claim 8. 10. A method for the prevention and treatment of tuberculosis by administering to a person or animal a drug according to claim 8 or a therapeutic cocktail according to claim 9.