Imidazoheterocyclic compounds processes for preparation thereof and pharmaceutical compositions comprising them

Claim 2

Imidazoheterocyclic compounds of the formula: wherein R 1 is (C 2 - C 6 ) alkenyl, (C 2 - C 6 ) alkynyl, (C 3 - C 6 ) alkadienyl, (C 2 - C 6 ) alkenyloxy (Ci - C 6 ) alkyl, (C 2 - C 6 ) alkynyloxy (Ci - C 6 ) alkyl, carboxy (C 2 - C 6 ) alkynyloxy (C 1 - C 6 ) alkyl or (Ci - C 6 ) alkoxycarbonyl (C 2 - C 6 ) alkynyloxy-(C 1 - C 6 ) alkyl, R 2 is hydrogen, (C 1 - C 6 ) alkyl or aryl selected from a group consisting of phenyl, tolyl, xylyl, 1-naphthyl, 2-naphthyl, 1-anthryl and 2-anthryl, R 3 is ar (C 1 - C 6 ) alkyl which has one or more suitable substituent(s) selected from a group consisting of (C 1 - C 6 ) alkyl and halogen, ar (C 2 - C 6 ) alkenyl, benzene-condensed cyclo (C s - C 6 ) alkyl, (C 1 - C 6 ) alkyl having cyclo (C 3 - C 6 ) alkyl or (Ci - C 6 ) alkyl, and X is O or NH, and a pharmaceutically acceptable salt thereof.

Claim 3

A compound of claim 1, wherein R 1 is (C 2 - C 6 ) alkenyl, (C 2 - C 6 ) alkynyl, (C 3 - C 6 ) alkadienyl, (C 2 - C 6 ) alkenyloxy (Ci - C 6 ) alkyl, (C 2 - C 6 ) alkynyloxy (Ci - C 6 ) alkyl, carboxy (C 2 - C 6 ) alkynyloxy (C i - C 6 ) alkyl or (Ci - C 6 ) alkoxycarbonyl (C 2 - C 6 ) alkynyloxy (Ci - C 6 ) alkyl and R 3 is ar (C 1 - C 6 ) alkyl which has one or more suitable substituent(s) selected from a group consisting of (C 1 - C 6 ) alkyl and halogen, ar (C 2 - C 6 ) alkenyl, benzene-condensed cyclo (Cs - C 6 ) alkyl, (C 1 - C 6 ) alkyl having cyclo (C 3 - C 6 ) alkyl or (Ci - C 6 ) alkyl.

Claim 4

A compound of claim 2, wherein R 3 is ar (C 1 - C 6 ) alkyl which has one or more suitable substituent(s) selected from a group consisting of (C 1 - C 6 ) alkyl and halogen.

Claim 5

A compound of claim 3, wherein R 3 is phenyl (C 1 - C 6 ) alkyl or naphthyl (C 1 - C 6 ) alkyl, each of which has 1 to 3 suitable substituent(s) selected from a group consisting of (Ci - C 6 ) alkyl and halogen.

Claim 6

A compound of claim 4, wherein R 1 is allyl, 2-propynyl, 1,2-propadienyl, allyloxymethyl, 2-propynyloxymethyl, 3-carboxy-2-propynyloxymethyl or 3-ethoxycarbonyl-2-propynyloxymethyl, R 2 is hydrogen, methyl or phenyl, and R 3 is benzyl which has 1 or 2 suitable substituent(s) selected from a group consisting of methyl, ethyl, isopropyl, fluoro, chloro and bromo.

Claim 7

A compound of claim 5, which is selected from a group consisting of: 8-(2-methylbenzyloxy)-3-(2-propynyl)-2-methylimidazo[1,2-a]-pyridine, 8-(2-ethylbenzyloxy)-3-(2-propynyl)-2-methylimidazo[1,2-a]-pyridine, 8-(2-isopropylbenzyloxy)-3-(2-propynyl)-2-methylimidazo-[1,2-a]-pyridine, 8-(2-chlorobenzyloxy)-3-(2-propynyl)-2-methylimidazo[1,2-a]-pyridine, 8-(3-chlorobenzyloxy)-3-(2-propynyl)-2-methylimidazo[1,2-a]-pyridine, 8-(4-chlorobenzyloxy)-3-(2-propynyl)-2-methylimidazo[1,2-a]-pyridine, 8-(2-bromobenzyloxy)-3-(2-propynyl)-2-methylimidazo[1,2-a]-pyridine, 8-(2-fluorobenzyloxy)-3-(2-propynyl)-2-methylimidazo-[1,2-a]pyridine, 8-(2,6-dimethylbenzyloxy)-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine, 8-(2,6-dichlorobenzyloxy)-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine, 8-(2-methylbenzylamino)-3-(2-propynyl)-2-methylimidazo[1,2a]pyridine, 8-(2-chlorobenzylamino)-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine, 8-(2-methylbenzyloxy)-3-(1,2-propadienyl)-2-methylimidazo[1,2-a] pyridine, 8-(2-methylbenzyloxy)-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine, 8-(2-chlorobenzyloxy)-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine, 8-(3-chlorobenzyloxy)-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine, 8-(4-chlorobenzyloxy)-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine, 8-(2-bromobenzyloxy)-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine, 8-(2,6-dichlorobenzyloxy)-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine, 8-(3,4-dichlorobenzyloxy)-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine, 8-(2,4-dichlorobenzyloxy)-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine, 8-(2-methylbenzylamino)-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine hydrochloride, 8-(2-chlorobenzylamino-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine hydrochloride.

Claim 8

A compound of claim 2, wherein R 1 is (C 2 - C 6 ) alkynyl, R 2 is (C 1 - C 6 ) alkyl, R 3 is phenyl (C 2 - C 6 ) alkenyl, 1,2,3,4-tetrahydronaphthyl, (C 1 - C 6 ) alkyl having cyclo (C 3 - C 6 ) alkyl or (C 1 - C 6 ) alkyl, and X is O.

Claim 9

A compound of claim 7, wherein R 1 is 2-propynyl, R 2 is methyl and R 3 is cinnamyl, 1,2,3,4-tetrahydro-1-naphthyl, cyclohexylmethyl or ethyl.

Claim 10

A compound of claim 8, which is selected from a group consisting of: 8-(cinnamyloxy)-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine, 8-(1,2,3,4-tetrahydro-l -naphthyloxy)-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine, 8-cyclohexylmethoxy-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine, and 8-ethoxy-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine.

Claim 11

A process for preparing imidazoheterocyclic compounds of the formula: wherein R 1 is (C 2 - C 6 ) alkenyl, (C 2 - C 6 ) alkynyl, (C 3 - C 6 ) alkadienyl, (C 2 - C 6 ) alkenyloxy (Ci - C 6 ) alkyl, (C 2 - C 6 ) alkynyloxy (Ci - C 6 ) alkyl, carboxy (C 2 - C 6 ) alkynyloxy (C 1 - C 6 ) alkyl or (C 1 - C 6 ) alkoxycarbonyl (C 2 - C 6 ) alkynyloxy-(C 1 - C 6 ) alkyl, R 2 is hydrogen, (C 1 - C 6 ) alkyl or aryl selected from a group consisting of phenyl, tolyl, xylyl, 1-naphthyl, 2-naphthyl, 1-anthryl and 2-anthryl, R 3 is ar (C 1 - C 6 ) alkyl which has one or more suitable substituent(s) selected from a group consisting of (C 1 - C 6 ) alkyl and halogen, ar (C 2 - C 6 ) alkenyl, benzene-condensed cyclo (C s - C 6 ) alkyl, (C 1 - C 6 ) alkyl having cyclo (C 3 - C 6 ) alkyl or (Ci - C 6 ) alkyl, and X is O or NH or a salt thereof, which comprises reacting a compound of the formula: wherein R 3 and X are each as defined above, or a salt thereof, with a compound of the formula: wherein R 1 and R 2 are each as defined above, and Z 1 is an acid residue selected from a group consisting of halogen and acyloxy, or a salt thereof.

Claim 12

A process for preparing imidazoheterocyclic compounds of the formula: wherein R 1 is (C 2 - C 6 ) alkenyl, (C 2 - C 6 ) alkynyl, (C 3 - C 6 ) alkadienyl, (C 2 - C 6 ) alkenyloxy (Ci - C 6 ) alkyl, (C 2 - C 6 ) alkynyloxy (Ci - C 6 ) alkyl, carboxy (C 2 - C 6 ) alkynyloxy (C 1 - C 6 ) alkyl or (C 1 - C 6 ) alkoxycarbonyl (C 2 - C 6 ) alkynyloxy-(C 1 - C 6 ) alkyl, R 2 is hydrogen, (C 1 - C 6 ) alkyl or aryl selected from a group consisting of phenyl, tolyl, xylyl, 1-naphthyl, 2-naphthyl, 1-anthryl and 2-anthryl, R 3 is ar (C 1 - C 6 ) alkyl which has one or more suitable substituent(s) selected from a group consisting of (C 1 - C 6 ) alkyl and halogen, ar (C 2 - C 6 ) alkenyl, benzene-condensed cyclo (C s - C 6 ) alkyl, (C 1 - C 6 ) alkyl having cyclo (C 3 - C 6 ) alkyl or (Ci - C 6 ) alkyl, and X is O or NH or a salt thereof, which comprises reacting a compound of the formula: wherein R 3 and X are each as defined above, or a salt thereof, with a compound of the formula: wherein R 1 and R 2 are each as defined above, and Z 1 is an acid residue selected from a group consisting of halogen and acyloxy, or a salt thereof.

Claim 13

A process for preparing imidazoheterocyclic compounds of the formula: wherein R 2 , R 3 and X are each as defined in claim 10, and R 1 b is cumulated (C 3 - C 6 ) alkadienyl, or a salt thereof, which comprises subjecting a compound of the formula: wherein R 2 , R 3 and X are each as defined in claim 10, and R 1 a is (C 2 - C 6 ) alkynyl, or a salt thereof, to isomerization reaction.

Claim 14

A process for preparing imidazoheterocyclic compounds of the formula: wherein R 2 , R 3 and X are each as defined in claim 10, R 4 is (C 2 - C 6 ) alkylene, and R 5 is (C 2 - C 6 ) alkenyl, (C 2 - C 6 ) alkynyl, carboxy (C 2 - C 6 ) alkynyl or (Ci - C 6 ) alkoxycarbonyl-(C 2 - C 6 ) alkynyl, or a salt thereof, which comprises reacting a compound of the formula: wherein R 2 , R 3 , R 4 and X are each as defined above, Z 2 is a leaving group, or a salt thereof, with a compound of the formula: R 5 -OH wherein R 5 is as defined above, or a salt thereof.

Claim 15

A process for preparing imidazoheterocyclic compounds of the formula: wherein R 2 , R 3 and X each as defined in claim 10, R' d is carboxy (C 2 - C 6 ) alkynyloxy (Ci - C 6 ) alkyl, in which the triple bond always exists on the terminal carbon atom of the (C 2 - C 6 ) alkyl moiety and this (C 2 - C 6 ) alkynyloxy-(C 1 - C 6 ) alkyl is substituted with carboxy on the terminal carbon atom of the (C 2 - C 6 ) alkynyl moiety, or (C i - C 6 ) alkoxycarbonyl (C 2 - C 6 ) alkynyloxy (Ci - C 6 ) alkyl, in which the triple bond always exists on the terminal carbon atom of the (C 2 - C 6 ) alkynyl moiety and this (C 2 - C 6 ) alkynyloxy (C i - C 6 ) alkyl is substituted with (C 1 - C 6 ) alkoxycarbonyl on the terminal carbon atom of the (C 2 -C 6 ) alkynyl moiety, or a salt thereof, which comprises subjecting a compound of the formula: wherein R 2 , R 3 and X are each as defined in claim 10, and R' c is (C 2 - C6) alkynyloxy (Ci - C 6 ) alkyl, in which the triple bond always exists on the terminal carbon atom of the (C 2 - C 6 ) alkynyl moiety, or a salt thereof, to acylation reaction.

Claim 16

A pharmaceutical composition which comprises, as an active ingredient, a compound of claim 1 or a pharmaceutically acceptable salt thereof in admixture with pharmaceutically acceptable carriers.

Claim 17

A compound of claim 1 or pharmaceutically acceptable salts thereof for use as a medicament.

Claim 18

A compound of claim 1 or pharmaceutically acceptable salts thereof for use in treating ulcer.

Claim 19

A compound of claim 1 or pharmaceutically acceptable salts thereof for the manufacture of a medicament for treating ulcer.