Naphthyridine derivatives

Claim 2

A heterocyclic compound of the formula: ##STR10## wherein the pyrroline ring and the symbols X 1 and X 2 together form an isoindoline nucleus or an isoindoline nucleus substituted by one or two atoms or radicals selected from halogen, alkyl of 1 through 4 carbon atoms, alkoxy of 1 through 4 carbon atoms, nitro and trifluoromethyl; the symbols Y 1 and Y 2 each represent hydrogen, halogen, alkyl of 1 through 4 carbon atoms, or alkoxy of 1 through 4 carbon atoms, and the symbols R 1 and R 2 each represent hydrogen; alkyl of 1 through 12 carbon atoms; alkyl of 1 through 12 carbon atoms substituted by a member of the class consisting of hydroxy, alkoxy of 1 through 4 carbon atoms, amino, monoalkylamino of which the alkyl radical has 1 through 4 carbon atoms, dialkylamino of which each alkyl radical has 1 through 4 carbon atoms or the alkyl radicals together with the nitrogen atom to which they are attached form a saturated five- or six-membered heterocyclic ring, and alkoxycarbonyl of which the alkoxy radical has 1 through 4 carbon atoms; alkenyl of 3 or 4 carbon atoms; alkynyl of 3 or 4 carbon atoms; or cycloalkyl of 3 through 6 carbon atoms, and when appropriate non-toxic pharmaceutically acceptable acid addition salts thereof.

Claim 3

A heterocyclic compound according to claim 1 wherein the halogen atom(s) referred to is (or are) chlorine.

Claim 4

A heterocyclic compound according to claim 1 which is 2-(7-chloro-1,8-naphthyridin-2-yl)-3-methylaminocarbonyloxy-isoindolin-1-one.

Claim 5

A heterocyclic compound according to claim 1 which is 2-(7-chloro-1,8-naphthyridin-2-yl)-3-n-butylaminocarbonyloxy-isoindolin-1-one.

Claim 6

A heterocyclic compound according to claim 1 which is 2-(7-chloro-1,8-naphthyridin-2-yl)-3-ethylaminocarbonyloxy-isoindolin-1-one.

Claim 7

A heterocyclic compound according to claim 1 which is 2-(7-chloro-1,8-naphthyridin-2-yl)-3-propylaminocarbonyloxy-isoindolin-1-one.

Claim 8

A heterocyclic compound according to claim 1 which is 2-(7-chloro-1,8-naphthyridin-2-yl)-3-sec-butylaminocarbonyloxy-isoindolin-1-one.

Claim 9

A heterocyclic compound according to claim 1 which is 2-(7-chloro-1,8-naphthyridin-2-yl)-3-pentylaminocarbonyloxy-isoindolin-1-one.

Claim 10

A heterocyclic compound according to claim 1 which is 2-(7-chloro-1,8-naphthyridin-2-yl)-3-cyclopropylaminocarbonyloxy-isoindolin-1-one.

Claim 11

A heterocyclic compound according to claim 1 which is 2-(7-chloro-1,8-naphthyridin-2-yl)-3-cyclohexylaminocarbonyloxy-isoindolin-1-one.

Claim 12

A heterocyclic compound according to claim 1 which is 2-(7-chloro-1,8-naphthyridin-2-yl)-3-cyclopentylaminocarbonyloxy-isoindolin-1-one.

Claim 13

A heterocyclic compound according to claim 1 which is 2-(7-chloro-1,8-naphthyridin-2-yl)-3-allylaminocarbonyloxy-isoindolin-1-one.

Claim 14

A heterocyclic compound according to claim 1 which is 2-(7-chloro-1,8-naphthyridin-2-yl)-3-n-hexylaminocarbonyloxy-isoindolin-1-one.

Claim 15

A heterocyclic compound according to claim 1 which is 2-(7-chloro-1,8-naphthyridin-2-yl)-3-dimethylaminocarbonyloxy-isoindolin-1-one.

Claim 16

A heterocyclic compound according to claim 1 which is 2-(7-chloro-1,8-naphthyridin-2-yl)-3-isobutylaminocarbonyloxy-isoindolin-1-one.

Claim 17

A heterocyclic compound according to claim 1 which is 2-(7-chloro-1,8-naphthyridin-2-yl)-3-diethylaminocarbonyloxy-isoindolin-1-one.

Claim 18

A heterocyclic compound according to claim 1 which is 2-(7-chloro-1,8-naphthyridin-2-yl)-3-(N-methyl-N-ethylaminocarbonyloxy)-isoindolin-1-one.

Claim 19

A heterocyclic compound according to claim 1 which is 2-(7-chloro-1,8-naphthyridin-2-yl)-3-(N-methyl-N-propylaminocarbonyloxy)-isoindolin-1-one.

Claim 20

A heterocyclic compound according to claim 1 which is 2-(7-chloro-1,8-naphthyridin-2-yl)-3-(N-butyl-N-methylaminocarbonyloxy)-isoindolin-1-one.

Claim 21

A heterocyclic compound according to claim 1 which is 2-(7-chloro-1,8-naphthyridin-2-yl)-3-N,N-dibutylaminocarbonyloxy-isoindolin-1-one.

Claim 22

A heterocyclic compound according to claim 1 which is 2-(7-chloro-1,8-naphthyridin-2-yl)-3-(N-methyl-N-pentylaminocarbonyloxy)-isoindolin-1-one.

Claim 23

A heterocyclic compound according to claim 1 which is 2-(7-chloro-1,8-naphthyridin-2-yl)-3-(2-diethylaminoethylamino)carbonyloxy-isoindolin-1-one.

Claim 24

A heterocyclic compound according to claim 1 wherein the pyrroline ring and the symbols X 1 and X 2 form an isoindoline nucleus or an isoindoline nucleus substituted by trifluoromethyl; Y 1 represents chlorine in the 7-position of the 1,8-naphthyridin-2-yl nucleus; Y 2 represents hydrogen; R 1 represents alkyl of 1 through 6 carbon atoms, alkyl of 1 through 6 carbon atoms substituted by alkyl of 1 through 6 carbon atoms substituted by alkoxy of 1 through 4 carbon atoms; and R 2 represents hydrogen or alkyl of 1 through 4 carbon atoms.

Claim 25

A heterocyclic compound according to claim 1 which is 2-(7-chloro-1,8-naphthyridin-2-yl)-3-(2-methoxyethyl)-aminocarbonyloxy-isoindolin-1-one.

Claim 26

A heterocyclic compound according to claim 1 which is 3-n-butylaminocarbonyloxy-2-(7-chloro-1,8-naphthyridin-2-yl)-5-trifluoromethyl-isoindolin-1-one.

Claim 27

A pharmaceutical composition which comprises, as an active ingredient, at least one heterocyclic compound as claimed in claim 1, or a non-toxic pharmaceutically acceptable acid addition salt thereof, in association with a significant amount of a pharmaceutical carrier.

Claim 28

A heterocyclic compound of the formula: ##STR11## wherein the pyrroline ring and the symbols X 1 and X 2 together form an isoindoline nucleus or an isoindoline nucleus substituted by one or two atoms or radicals selected from halogen, alkyl of 1 through 4 carbon atoms, alkoxy of 1 through 4 carbon atoms, nitro and trifluoromethyl; the symbols Y 1 and Y 2 each represent hydrogen, halogen, alkyl of 1 through 4 carbon atoms, or alkoxy of 1 through 4 carbon atoms, and the symbols R 1 and R 2 each represent hydrogen; alkyl of 1 through 12 carbon atoms; alkyl of 1 through 12 carbon atoms substituted by a member of the class consisting of hydroxy, alkoxy of 1 through 4 carbon atoms, amino, monoalkylamino of which the alkyl radical has 1 through 4 carbon atoms, dialkylamino of which each alkyl radical has 1 through 4 carbon atoms or the alkyl radicals together with the nitrogen atom to which they are attached form a saturated five- or six-membered heterocyclic ring, and alkoxycarbonyl of which the alkoxy radical has 1 through 4 carbon atoms; alkenyl of 3 or 4 carbon atoms; alkynyl of 3 or 4 carbon atoms; or cycloalkyl of 3 through 6 carbon atoms, or R 1 and R 2 together with the nitrogen atom to which they are attached form a piperidino or pyrrolidino ring, and when appropriate non-toxic pharmaceutically acceptable acid addition salts thereof."

Claim 29

A heterocyclic compound of the formula: ##STR11## wherein the pyrroline ring and the symbols X 1 and X 2 together form an isoindoline nucleus or an isoindoline nucleus substituted by one or two atoms or radicals selected from halogen, alkyl of 1 through 4 carbon atoms, alkoxy of 1 through 4 carbon atoms, nitro and trifluoromethyl; the symbols Y 1 and Y 2 each represent hydrogen, halogen, alkyl of 1 through 4 carbon atoms, or alkoxy of 1 through 4 carbon atoms, and the symbols R 1 and R 2 each represent hydrogen; alkyl of 1 through 12 carbon atoms; alkyl of 1 through 12 carbon atoms substituted by a member of the class consisting of hydroxy, alkoxy of 1 through 4 carbon atoms, amino, monoalkylamino of which the alkyl radical has 1 through 4 carbon atoms, dialkylamino of which each alkyl radical has 1 through 4 carbon atoms or the alkyl radicals together with the nitrogen atom to which they are attached form a saturated five- or six-membered heterocyclic ring, and alkoxycarbonyl of which the alkoxy radical has 1 through 4 carbon atoms; alkenyl of 3 or 4 carbon atoms; alkynyl of 3 or 4 carbon atoms; or cycloalkyl of 3 through 6 carbon atoms, or R 1 and R 2 together with the nitrogen atom to which they are attached form a piperidino or pyrrolidino ring, and when appropriate non-toxic pharmaceutically acceptable acid addition salts thereof."

Claim 30

A heterocyclic compound according to claim 27 which is 2-(7-chloro-1,8-naphthyridin-2-yl)-3-piperidinocarbonyloxy-isoindolin-1-one.

Claim 31

Pharmaceutical compositions which comprise, as an active ingredient, at least one heterocyclic compound as claimed in claim 27, or -- when appropriate -- a non-toxic pharmaceutically acceptable acid addition salt thereof, in association with a significant amount of a pharmaceutical carrier.