1,9-diazabicyclo[4.3.0]nona-3,8-diene derivatives

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

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Details

514210, 5142332, 514253, 546121, 544127, 544362, A61K 31437, A61K 31496, C07D22100, C07D47104

Patent

active

060807555

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to diazabicyclo compounds and pharmaceutically acceptable salts thereof and more particularly, to novel 1,9-diazabicyclo-[4.3.0]nona-3,8-diene derivatives and pharmaceutically acceptable salts thereof. Furthermore, the present invention relates to cardiovascular agents containing the diazabicyclo compounds or pharmaceutically acceptable salts thereof as an active ingredient.


INDUSTRIAL APPLICABILITY

The diazabicyclo compounds of the present invention are novel compounds having, as a basic skeleton, 1,9-diazabicyclo[4.3.0]nonan represented by the following formula (A): ##STR2## wherein the dotted line shows either double bond or single bond.
Accordingly, a first aspect of the present invention is to provide novel 1,9-diazabicyclo[4.3.0]-nona-3,8-diene compounds represented by the following formula (I): ##STR3## wherein R.sup.1 is a group selected from the following: (1) lower alkyl group or lower alkenyl group which may be substituted by cyano, nitro, lower alkylthio, lower alkylsulfinyl or lower alkylsulfonyl group, alkoxycarbonyl group, and atoms or phenyl groups which may be substituted by halogen, cyano, lower alkyl, lower alkoxy, nitro, aryl or lower acyl group, and atoms or lower alkyl groups,
Specifically, the present invention provides 1,9-diazabicyclo[4.3.0]nona-3,8-diene compounds represented by the following formula (I-a): ##STR4## wherein R.sup.a is a lower alkyl group, and above,
More specifically, the present invention provides 1,9-diazabicyclo[4.3.0]nona-3,8-diene compounds represented by the following formula (I-b): ##STR5## wherein R.sup.a, R.sup.1, R.sup.4 and R.sup.7 have the same meanings as above,
Still more specifically, the present invention provides 1,9-diazabicyclo[4.3.0]nona-3,8-diene compounds represented by the following formula (I-c): ##STR6## wherein R.sup.a, R.sup.1, R.sup.5 and R.sup.6 have the same meanings as above,
A second aspect of the present invention is to provide cardiovascular agents comprising, as an active ingredient, said 1,9-diazabicyclo[4.3.0]nona-3,8-diene compounds or pharmaceutically acceptable salts thereof.
A third aspect of the present invention is to provide the use of said 1,9-diazabicyclo[4.3.0]-nona-3,8-diene compounds or pharmaceutically acceptable salts thereof as a medicament, or a method for the treatment of cardiovascular diseases in human being.


DETAILED DESCRIPTION OF THE INVENTION

It is to be understood that when the compounds of the present invention have one or more asymmetric carbon(s), those optically active compounds can be obtained by resolution of the diastereoisomeric mixture of these compounds by ordinary methods (see Examples mentioned later). Therefore, the optically active compounds and stereoisomeric mixture of the compounds should be included within the scope of the compounds of the present invention.
The compounds of the present invention may be converted to pharmaceutically acceptable acid addition salts thereof with an organic or inorganic acid. Examples of the organic acid include aliphatic acid such as formic acid, acetic acid, propionic acid, butyric acid, trifluoroacetic acid, trichloroacetic acid and the like; substituted or unsubstituted benzoic acid such as benzoic acid, p-nitrobenzoic acid and the like; lower-(halo)alkylsulfonic acid such as methanesulfonic acid, trifluoromethanesulfonic acid and the like; substituted or unsubstituted arylsulfonic acid such as benzenesulfonic acid, p-nitrobenzenesulfonic acid, p-bromobenzenesulfonic acid, toluenesulfonic acid, 2,4,6-triisopropylbenzenesulfonic acid and the like; and organic phosphoric acid such as diphenylphosphate. Examples of the inorganic acid include hydrochloric acid, sulfuric acid, hydrobromic acid, hydroiodic acid, borofluoric acid, perchloric acid, nitrous acid and the like.
Typical examples of the compounds of the present invention are as follows: (Compound No. 29); [4.3.0]nona-3,8-dien-7-ol (Compound No. 31); [4.3.0]nona-3,8-dien-7-ol (Compound No. 35); 4)-methybicyclo[4.3.0]-1,9-diazanona-3,8-dien-7-ol (Co

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