DNA gyrase inhibitors and pharmaceutical preparations therefor

Details DNA gyrase inhibitors and pharmaceutical preparations therefor DNA gyrase inhibitors and pharmaceutical preparations therefor

1992-12-09

1994-03-15

Shah, Mukund J.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

540455, 460 12, 460 18, 562451, 4352535, C07D29108, A61K 31395

Patent

active

052946096

DESCRIPTION:

BRIEF SUMMARY
The invention relates to novel DNA gyrase inhibitors, which are bicyclic derivatives of the general formula ##STR2## wherein X.sup.1 is --S-- or --SO--; halogen or lower alkoxy; amino, lower alkylamino, di-lower alkylamino, acylamino, lower alkoxy, lower alkoxymethoxy or a group OR.sup.4 ; (thio)carboxy, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted acyl or heterocyclyl; in which R is hydrogen or lower alkyl, A is hydrogen, optionally substituted alkyl, lower cycloalkyl, iminoyl, (thio)acyl, esterified carboxy or amidated (thio)carboxy and B is lower alkylidene; alkoxycarbonylmethylidene or optionally substituted hydroxyimino; and carboxy or amidated (thio)carboxy; provided that no more than two of R.sup.1 -R.sup.3 are nitrogen-containing groups; no more than two of R.sup.1 -R.sup.3 are oxygen containing groups and no more than two of R.sup.1 -R.sup.3 are either nitrogen containing or oxygen containing groups; carrying an acidic and/or basic substituent.
Hereinabove and in the following, reference to the word "lower" such as in "lower alkyl", "lower alkoxy", "lower alkanoyl" etc. refers to hydrocarbon groups containing up to and including 6, preferably 1-2, carbon atoms unless otherwise specified. Thus, e.g. "lower alkyl" in the following, alone or in combination with other groups such as in "lower alkylamino", "di-lower alkylamino", "aryl-lower alkyl" etc. is e.g. methyl, ethyl, t-butyl, n-pentyl etc.; "lower alkoxy" has analogous meanings; "lower alkenyl" alone or in combination with other groups such as "lower cycloalkyl-lower alkenyl", "heterocyclyl-lower alkenyl" etc. is e.g. vinyl, 1- or 2-propenyl; "lower cycloalkyl" alone or in combination with other groups such as "lower cycloalkyl-lower alkenyl", "lower cycloalkyl-lower alkyl" etc. is e.g. cyclopropyl, cyclobutyl, cyclohexyl; "lower alkynyl" alone or in combination with other groups such as "lower cycloalkyl-lower alkynyl" is e.g. ethynyl, 1- or 2-propynyl; "lower alkanoyl" alone or in combination with other groups such as "lower alkanoyloxy" etc. is e.g. formyl, acetyl, propionyl, isobutyryl, pivaloyl etc.
Groups not specified by the word "lower", such as "alkyl", "alkoxy", "alkenyl", "acyl" and "alkanoyl", are intended to refer to groups containing up to and including 14 carbon atoms unless otherwise specified.
"(Thio)acyl" refers to an acyl group or a thioacyl group.
"Acyl" alone or in combination with other groups such as in "acylamino", is preferably derived from a carboxylic acid and is thus e.g. lower alkanoyl, e.g. formyl, acetyl, propionyl, isobutyryl, pivaloyl; lower alkenoyl, e.g. crotonoyl, isocrotonoyl; lower cycloalkanoyl, e.g. cyclopropylcarbonyl; aroyl, e.g. benzoyl, o-carboxy-benzoyl, p-toluoyl, p-anisoyl, naphthoyl; heterocyclylcarbonyl, e.g. furoyl, thenoyl. "Thioacyl" has analogous meanings.
"Halogen" alone or in combination with other groups such as in "halogen-lower alkyl" etc. refers to all four halogens, i.e. chlorine, bromine, iodine, fluorine, unless otherwise indicated.
The expressions "lower alkenylalkyl" and "lower alkynylalkyl" are employed to indicate that the double and triple bonds of these groups are not connected with the first carbon atom (such as in vinyl, ethynyl and 1-propynyl), but that these groups are limited to the less reactive groups having their unsaturation in 2-, 3- and further positions. It is understood that "lower alkenylalkyl" and "lower alkynylalkyl" refer to groups containing up to and including 5 carbon atoms, e.g. 2-propenyl, 2-butenyl, 3-butenyl, 2-methyl-2-propenyl, 2-propynyl, 2-butynyl, 3-butynyl, 2-methyl-2-propynyl.
Easily hydrolyzable groups --OR.sup.4 are e.g. lower alkanoyloxy groups such as formyloxy, acetoxy, propionyloxy, isobutyryloxy, pivaloyloxy or lower alkoxycarbonyloxy groups such as methoxycarbonyloxy or ethoxycarbonyloxy.
The above definition of R.sup.1 -R.sup.3 signifies that no more than two of these substituents are nitrogen-containing groups, i.e. amino, lower alkylamino, di-lower alkylamino and/or acylamino; moreover, no more th

REFERENCES:
patent: 3239350 (1966-03-01), Hodge et al.

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