# US 5,708,171 A · Imidazole derivatives for pharmaceutical use

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- Number: US 5,708,171 A
- Document ID: US5708171A
- Status: Granted
- Kind: A
- Application number: 08/663,679
- Filed: 1996-06-14
- Granted: 1998-01-13
- Earliest claimed: 1992-01-10
- Assignees: Institut National de la Sante et de la Recherche Medicale; Societe Civile Bioprojet
- Inventors: Jean-Charles Schwartz; Jean-Michel Arrang; Monique Garbarg; Jeanne-Marie Lecomte; Charon Robin Ganellin; Abdellatif Fkyerat; Wasyl Tertiuk; Walter Schunack; Ralph Lipp; Holger Stark; Katja Purand
- Web page: https://patentgrep.com/patent/US5708171A

## CPC

- C07D 233/64: with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
- A61P 1/04: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/08: Antiepileptics; Anticonvulsants
- A61P 25/20: Hypnotics; Sedatives
- A61P 25/24: Antidepressants
- A61P 25/26: Psychostimulants, e.g. nicotine, cocaine
- A61P 35/00: Antineoplastic agents
- A61P 37/08: Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14)
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 233/84: Sulfur atoms
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 403/12: linked by a chain containing hetero atoms as chain links
- C07D 417/12: linked by a chain containing hetero atoms as chain links
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

A compound selected from the group consisting of a compound of the formula ##STR1## having antagonist properties to histamine H.sub.3 -receptors.

## Claims

### Claim 1

A medicament acting as an antagonist of the H.sub.3 receptors of histamine containing a compound selected from the group consisting of a compound of the formula ##STR198## in which A is a hydrocarbon chain containing 1 to 6 carbon atoms uninterrupted or interrupted by a heteroatom selected from the group consisting of --S--, --O-- and --NH--; X is selected from the group consisting of oxygen, sulfur, --CO--, --NH--, --NHCO--, --N(alkyl)CO--, NHCONH--, --NHCS--, --O--CO--, --CO--O--, --OCONH--, --OCON(alkyl)--, --OCONH-- --CONH--, --CON(alkyl)--, --SO--, --CHOH-- and --NR--C(.dbd.NR")--NR'--; R and R' are hydrogen or lower alkyl; and R" is selected from the group consisting of hydrogen, cyano and --COY.sub.1, Y.sub.1 is alkoxy; B is selected from the group consisting of --(CH.sub.2).sub.n --, n is an integer from 0 to 5, a branched alkylene of 2 to 8 carbon atoms uninterrupted or interrupted by at least one oxygen or sulfur, --(CH.sub.2).sub.n --O--, and --(CH.sub.2).sub.n' --S--, where n' is an integer of 1 or 2; Y is selected from the group consisting of alkyl of 1 to 8 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, bicycloalkyl, cycloalkenyl, aryl, 5- or 6-membered heterocycle selected from the group consisting of pyridyl, N-oxide-pyridyl, pyrimidinyl, and pyrazinyl unsubstituted or substituted with at least one member of the group consisting of --NO.sub.2, --CF.sub.3, --CH.sub.3, --NH.sub.2, halogen, --COOCH.sub.3, imidazolyl, thiazolyl, and a bicyclic formed by a heterocycle as defined above to which a phenyl ring is fused;
with the proviso that, when X is --NH-- and A is a straight saturated hydrocarbon chain containing 1 to 6 carbon atoms, B cannot be a straight alkylene chain and Y cannot be phenyl or imidazolyl;
with the proviso that, when X is --NH-- and A is --(CH.sub.2).sub.2 --, B and Y cannot simultaneously be --(CH.sub.2).sub.2 --O-- or --(CH.sub.2).sub.n --S-- and phenyl or p-chlorophenyl;
with the proviso that when X is --NH-- and A is a straight saturated hydrocarbon chain of 1 to 6 carbon atoms, Y cannot be substituted or unsubstituted aryl (formula IB), and when X is --NH-- and A is --CH.sub.2 -- in formula IA, B and Y cannot simultaneously be --CH.sub.2 -- and 2,6-dimethylphenyl;
with the proviso that when X is --NH-- and A is --(CH.sub.2).sub.2 --, B and Y cannot simultaneously be --CH(C.sub.1 -C.sub.3 alkyl)--CH.sub.2).sub.n -- (n=1 to 4) and methyl or substituted or unsubstituted phenyl in formula IA and Y cannot be --(CH.sub.2)6-- in the formula IB;
with the proviso that, when X is --NHCONH-- and A is a straight saturated hydrocarbon chain of 1 to 6 carbon atoms, B and/or Y cannot be alkyl, and Y cannot be aryl;
with the proviso that, when X is --NHCO-- and A is --(CH.sub.2).sub.2 --, Y in formula IB cannot be methyl or substituted cyclohexyl, or Y cannot be para-nitrophenyl or para-amino-phenyl, B and Y in formula IA cannot simultaneously be --(CH.sub.2).sub.n --, n being an integer of 1 to 6, --CH.sub.2 --O--, or --CH.sub.2 S--CH.sub.2 -- and phenyl, or --CH.sub.2 --CH.sub.2 -- or --CH.sub.2 --S--CH.sub.2 -- and diphenyl or --(CH.sub.2).sub.3 -- or --CH.sub.2 --S--CH.sub.2 and pyridyl, or --CH.sub.2 --CH.sub.2 -- or --CH.sub.2 --S-- and diphenyl or --(CH.sub.2).sub.3 -- and imidazolyl or cyclohexyl;
with the proviso that, when X is --NHCO-- and A is --CH.sub.2 --CH(CH.sub.3)--, B and Y cannot simultaneously be --(CH.sub.2).sub.3 -- and phenyl;
with the proviso that, when X is --NHCONH-- and A is --(CH.sub.2).sub.2, B and Y cannot simultaneously be --CH.sub.2 --CH.sub.2 -- and phenyl;
with the proviso that, when X is oxygen and A is --CH.sub.2 --, Y in formula IB cannot be substituted phenyl;
with the proviso that, when X is --CO-- and A is --(CH.sub.2).sub.2 --, Y in formula IB cannot be substituted or unsubstituted aryl;
with the proviso that, when X is --CO-- and A is methylene, B and Y cannot simultaneously be --C(CH.sub.3).sub.2 --(CH.sub.2).sub.n -- (n=0 or 1) and substituted or unsubstituted aryl;
with the proviso that, when X is --CONH-- and A is --(CH.sub.2).sub.2 --, Y in formula IB cannot be substituted or unsubstituted phenyl;
with the proviso that, when X is --NH--C(.dbd.NCN)--NH--, A and B are hydrocarbon chains of 2 to 5 carbon atoms interrupted or uninterrupted by S or O, Y cannot be pyridyl, imidazolyl, or thiazolyl;
with the proviso that, when X is --NH--C(.dbd.NCN)--NH-- and A is --CH.sub.2 --S--(CH.sub.2).sub.2 --, Y in formula IB cannot be methyl;
with the proviso that, when X is --NH--C(.dbd.NH)--NH--, Y cannot be alkyl or aryl;
with the proviso that, when X is --NH--C(.dbd.NH)--NH--, A is --(CH.sub.2).sub.n -- (n=2 or 3), Y cannot be pyridyl, imidazolyl, benzimidazolyl or quinolyl in formula IA;
with the proviso that, when X is --NH--C--(.dbd.NCOY.sub.1)--NH-- and A is hydrocarbon of 2 to 5 carbon atoms interrupted by 0 or S, Y cannot be alkyl;
with the proviso that, when X is --NH--C(--NCOY.sub.1)--NH--, A is --(CH.sub.2).sub.n -- (n=2 or 3) and B is --(CH.sub.2).sub.n -- (n=2 to 5) or a branched alkylene chain of 3 to 6 carbon atoms optionally interrupted or uninterrupted by oxygen or sulfur, or --(CH.sub.2).sub.2 --O-- or (CH.sub.2).sub.2 --S--, Y cannot be substituted or unsubstituted aryl or pyridyl, imidazolyl, benzimidazolyl or quinolyl;
with the proviso that, when X is --NH--C(=NCOY.sub.1)--NH--, A is --(CH.sub.2).sub.n -- (n=2 or 3), Y in formula IB cannot be pyridyl;
with the proviso that, when X is NH and Y is alkyl, A is neither --(CH.sub.2).sub.2 -- nor --(CH.sub.2).sub.3 --;
and a pharmaceutically acceptable salt, hydrate, hydrated salt, polymorphic crystalline structures of the tautomeric forms thereof, in the presence or absence of a therapeutically acceptable vehicle or excipient.

### Claim 2 (depends on 1)

The medicament of claim 1 wherein A is --(CH.sub.2).sub.n -- and n is an integer from 0 to 6.

### Claim 3 (depends on 2)

The medicament of claim 2 wherein n is 1 to 4.

### Claim 4 (depends on 2)

The medicament of claim 2 wherein A is alkylene substituted with at least one methyl or ethyl.

### Claim 5 (depends on 1)

The medicament of claim 1 wherein Y is selected from the group consisting of cyclopentyl, cyclohexyl and bicycloalkyl.

### Claim 6 (depends on 1)

The medicament of claim 1 wherein Y is phenyl substituted with at least one member of the group consisting of halogen, lower alkyl, --CF.sub.3, --CN, --COCH.sub.3, --COOR.sub.1, --COR.sub.1, --OR.sub.1, --COOH, --NO.sub.2 ##STR199## R.sub.1 is alkyl and R.sub.2 and R.sub.3 are individually hydrogen or lower alkyl.

### Claim 7 (depends on 1)

The medicament of claim 1 wherein Y is benzothiazolyl.

### Claim 8 (depends on 1)

The medicament of claim 1 wherein A is a saturated hydrocarbon chain interrupted by a sulfur.

### Claim 9

A medicament acting as an antagonist of the H.sub.3 receptors of histamine containing a compound of the formula ##STR200## wherein A is a hydrocarbon of 2 to 6 carbon atoms, X is oxygen and Y is phenyl unsubstituted or substituted by at least one member of the group consisting of halogen, lower alkyl, --CF.sub.3 --CH, --COCH.sub.3, --COOR.sub.1, --OR.sub.1, --COR.sub.1, --COOH, --NO.sub.2 and ##STR201## R.sub.1 is lower alkyl and R.sub.2 and R.sub.3 are hydrogen or lower alkyl or a pharmaceutically acceptable salt, hydrate, hydrated salt, polymorphic crystalline structures or the tautomeric forms thereof, in the presence or absence of a therapeutically acceptable vehicle or excipient.

### Claim 10 (depends on 9)

The medicament of claim 9 wherein A is ethylene or propylene.

### Claim 11

A medicament acting as an antagonist of H.sub.3 receptors of histamine containing a compound selected from the group consisting of ##STR202## wherein A is a hydrocarbon of 1to 6 carbon atoms uninterrupted or interrupted by a heteroatom selected from the group consisting of oxygen, sulfur and --NH--; X is selected from the group consisting of --OCO--, --COO--, --OCOHN--, --OCON(alkyl)--, and --OCOHN--CO--; B is selected from the group consisting of --(CH.sub.2).sub.n --, n is an integer from 0 to 5, a branched alkylene of 2 to 8 carbon atoms uninterrupted or interrupted by at least one oxygen or sulfur, --(CH.sub.2).sub.n' --O-- and --(CH.sub.2).sub.n, --S-- wherein n' is an integer of 1 or 2; Y is selected from the group consisting of alkyl of 1 to 8 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, bicycloalkyl, cycloalkenyl, aryl, 5- or 6-membered heterocycle selected from the group consisting of pyridyl, N-oxide-pyridyl, pyrimidinyl and pyrazinyl unsubstituted or substituted with at least one member of the group consisting of --NO.sub.2 --, --CF.sub.3, --CH.sub.3, --NH.sub.2, halogen, --COOCH.sub.3, imidazolyl, thiazolyl, and a bicyclic formed by a heterocycle as defined above to which a phenyl ring is fused and a pharmaceutically acceptable salt, hydrate, hydrated salt, polymorphic crystalline structures, or tautomeric forms thereof, in the presence or absence of a therapeutically acceptable vehicle or excipient.

### Claim 12

A medicament acting as an antagonist of the H.sub.3 receptors of histamine containing a compound selected from the group consisting of ##STR203## wherein A is a hydrocarbon of 1 to 6 carbon atoms uninterrupted or interrupted by a heteroatom selected from the group consisting of oxygen, sulfur, and --NH--; X is selected from the group consisting of sulfur, oxygen, --N(alkyl)CO--, --NHCS--, --CON(alkyl)--, --SO--, and --CHOH--; B is selected from the group consisting of --(CH.sub.2).sub.n, n is an integer from 0 to 5, a branched alkylene of 2 to 8 carbon atoms uninterrupted or interrupted by at least one member of the group consisting of oxygen, sulfur, --(CH.sub.2).sub.n '--O-- and --(CH.sub.2).sub.n '--S--, where n' is an integer of 1 or 2; Y is selected from the group consisting of alkyl of 1 to 8 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, cycloalkyl, cycloalkenyl, aryl 5- or 6-membered heterocycle selected from the group consisting of pyridyl, n-oxide-pyridyl, pyrimidinyl, and pyrazinyl unsubstituted or substituted with at least one member of the group consisting of --NO.sub.2 --, --CF.sub.3, --CH.sub.3, --NH.sub.2, halogen, --COOCH.sub.3, imidazolyl, thiazolyl, and a bicyclic formed by said heterocycle as defined above to which a phenyl ring is fused provided that when X is oxygen and A is --CH.sub.2 --, Y in formula I.sub.B cannot be substituted phenyl, and a pharmaceutically acceptable salt, hydrate, hydrated salt, polymorphic crystalline structures, or tautomeric forms thereof, in the presence or absence of a therapeutically acceptable vehicle or excipient.

### Claim 13

A medicament acting as an antagonist of the H.sub.3 receptors of histamine containing a compound of the formula ##STR204## wherein A is a hydrocarbon of 1 to 6 carbon atoms, uninterrupted or interrupted by a heteroatom selected from the group consisting of oxygen, sulfur and nitrogen; X is ##STR205## R and R' are hydrogen or lower alkyl; R" is selected from the group consisting of hydrogen, cyano, and --COY.sub.1, Y.sub.1 is alkoxy; B is selected from the group consisting of --(CH).sub.n --, n is an integer from 0 to 5, a branched alkylene of 2 to 8 carbon atoms uninterrupted or interrupted by at least one oxygen or sulfur, --(CH.sub.2).sub.n '--O-- and --(CH.sub.2).sub.n, --S-- where n' is an integer of 1 or 2; Y is selected from the group consisting of cycloalkyl of 3 to 6 carbon atoms, bicycloalyl, cycloalkenyl, pyrimidinyl and pyrazinyl unsubstituted and substituted with at least one member of the group consisting of --NO.sub.2, --CF.sub.3, --CH.sub.3, --NH.sub.2, halogen and --COOCH.sub.3 with the proviso that when X is --NH--C(NCN)--NH--, A and B are hydrocarbon chains of 2 to 5 carbon atoms interrupted or uninterrupted by S or O, Y cannot be pyridyl, imidazolyl, or thiazolyl;
with the proviso that, when X is --NH--C(.dbd.NCN)--NH-- and A is --CH.sub.2 -- S--(CH.sub.2).sub.2 --, Y in formula IB cannot be methyl;
with the proviso that, when X is --NH--C(.dbd.NH)--NH--, Y cannot be alkyl or aryl;
with the proviso that, when X is --NH--C(.dbd.NH)--NH--, A is --(CH.sub.2).sub.n (n=2 or 3), Y cannot be pyridyl, imidazolyl, benzimidazolyl or quinolyl in formula IA;
with the proviso that, when X is --NH--C--(.dbd.NCOY.sub.1)--NH-- and A is hydrocarbon of 2 to 5 carbon atoms interrupted or uninterrupted by O or S, Y cannot be alkyl;
with the proviso that, when X is --NH--C--(NCOY.sub.1)--NH--, A is --(CH.sub.2).sub.n -- (n=2 or 3) and B is --(CH.sub.2).sub.n -- (n=2 to 5) or a branched alkylene chain of 3 to 6 carbon atoms optionally interrupted or uninterrupted by oxygen or sulfur, or --(CH.sub.2).sub.2 --O-- or (CH.sub.2)--S--, Y cannot be substituted or unsubstituted aryl or pyridyl, imidazolyl, benzimidazolyl or quinolyl;
with the proviso that, when X is --NH--C(.dbd.NCOY.sub.1)--NH--, A is --(CH.sub.2).sub.n -- (n=2 or 3), Y in formula IB cannot be pyridyl; and a pharmaceutically acceptable salt, hydrate, hydrated salt, polymorphic crystalline structures, or tautomeric forms thereof, in the presence or absence of a therapeutically acceptable vehicle or excipient.

### Claim 14 (depends on 1)

A medicament acting as an antagonist of the H.sub.3 receptors of histamine containing a compound according to claim 1 selected from the group consisting of:
N-((1H-Imidazol-4-yl)methyl)-5-phenylpentanamide,
N-(3-(1H-Imidazol-4-yl)propyl)-3-phenylpropanamide,
N-(3-(1H-Imidazol-4-yl)propyl)-3cyclohexylpropanamide,
N-(3-(1H-Imidazol-4-yl)propyl)-3-cyclopentylpropanamide,
N-(3-(1H-Imidazol-4-yl)propyl)-2-(4-chlorophenoxy)acetamide,
N-(3-(1H-Imidazol-4-yl)propyl)-2-cyclohexylacetamide,
N-(3-(1H-Imidazol-4-yl)propyl)-4-cyclohexylbutanamide,
N-(3-(1H-Imidazol-4-yl)propyl)-4-methylpentanamide,
N-(3-(1H-Imidazol-4-yl)propyl)-3,3-diphenylpropanamide,
N-(3-(1H-Imidazol-4-yl)propyl)-3-(bicyclo-›2.2.1!hept-2-yl)propanamide,
N-(3-(1H-Imidazol-4-yl)propyl)hexanamide,
N-(3-(1H-Imidazol-4-yl)propyl)heptanamide
N-(3-(1H-Imidazol-4-yl)propyl)octanamide,
N-(3-(1H-Imidazol-4-yl)propyl)-3-(2-cyclopenten-1-yl)propanamide,
(R,S)-(.+-.)-N-(3-(1H-Imidazol-4-yl)propyl)-3-phenylbutanamide,
N-(3-(1H-Imidazol-4-yl)propyl)-3-(2-pyrazinyl)propanamide,
N-(4-(1H-Imidazol-4-yl)butyl)-2-cyclopentylacetamide,
N-(4-(1H-Imidazol-4-yl)butyl)-3-cyclopentylpropanamide,
(E)-N-(3-(1H-Imidazol-4-yl)allyl)-3-cyclopentylpropanamide,
N-(3-Phenylpropyl)-3-(1H-imidazol-4-yl)propanamide,
N-(2-(1H-Imidazol-4-yl)ethyl)-4-cyclohexylbutanethioamide,
N-(3-(1H-Imidazol-4-yl)propyl)-3-cyclopentylpropanethioamide,
N-Benzyl-N'-(3-(1H-imidazol-4-yl)propyl)urea,
3-(1H-Imidazol-4-yl)propyl ester of 3-cyclopentylpropanoic acid,
3-(1H-Imidazol-4-yl)propyl ester of benzoic acid,
3-(1H-Imidazol-4-yl)propyl ester of 4-iodobenzoic acid,
3-(1H-Imidazol-4-yl)propyl ester of 3-iodobenzoic acid,
3-(1H-Imidazol-4-yl)propyl ester of 3-iodo-4-methylbenzoic acid,
3-(1H-Imidazol-4-yl)propyl ester of 3-(4-iodophenyl)propanoic acid,
3-(1H-Imidazol-4-yl)propyl ester of 4-amino-3,5-diiodobenzoic acid,
3-(1H-Imidazol-4-yl)propyl ester of 4-(4-iodophenyl)butanoic acid,
3-(1H-Imidazol-4-yl)propyl ester of 2-(4-iodophenyl)acetic acid,
3-(1H-Imidazol-4-yl)propyl ester of 4-phenylbutanoic acid,
3-(1H-Imidazol-4-yl)propyl N-benzylcarbamate,
3-(1H-Imidazol-4-yl)propyl N-(cyclohexylmethyl)carbamate,
3-Cyclohexylpropyl 3-(1H-imidazol-4-yl)propyl ether,
3-(3,4-Difluorophenyl)propyl 3-(1H-imidazol-4-yl)propyl ether,
3-(4-Bromophenyl)propyl 3-(1H-imidazol-4-yl)propyl ether,
3-(3-Trifluoromelthylphenyl)propyl 3-(1H-imidazol-4-yl)propyl ether,
1-Naphthylmethyl 3-(1H-imidazol-4-yl)propyl ether,
(4-Iodophenyl)methyl 3-(1H-imidazol-4-yl)propyl ether,
4-Phenylbutyl 3-(1H-imidazol-4-yl)propyl ether, (Z)-N-(3-(1H-Imidazol-4-yl)allyl)-3-cyclohexylpropanamide,
(R,S)-(.+-.)-N-(3-(1-Imidazol-4-yl)butyl)-3-cyclohexylpropanamide,
3-Phenylpropyl 3-(1H-imidazol-4-yl)propyl ether,
3-Phenylpropyl 3-(1H-imidazol-4-yl)propyl sulphide,
4-›(4-Nitrobenzylthio)methyl!-1H-imidazole,
3-Phenylpropyl 3-(1H-imidazol-4-yl)propyl sulphoxide,
1-(1H-Imidazol-4-yl)-7-phenylheptan-4-one,
1-(1H-Imidazol-4-yl)-7-phenylheptan-4-ol,
N-Cyano-N'-›3-(1H-imidazol-4-yl)propyl!-N"-cyclohexylmethylguanidine,
N-Ethoxycarbonyl-N'-›3-(1H-imidazol-4-yl)propyl!-N"-cyclohexylmethylguanidi ne,
N-(1,1-Dimethylethoxycarbonyl)-N'-›3-(1H-imidazol-4-yl)propyl!-N"-cyclohexy lmethylguanidine,
N-›3-(1H-Imidazol-4-yl)propyl!-N'-cyclohexylmethylguanidine,
3-(1H-imidazol-4-yl)propyl N-benzoylcarbamate,
3-(1H-Imidazol-4-yl)propyl N-(cyclobutylmethyl)carbamate,
3-(1H-Imidazol-4-yl)propyl -N-(cyclopropylmethyl)carbamate,
3-(1H-Imidazol-4-yl)propyl (R)-(+)-N-(1-phenylethyl)carbamate,
3-(1H-Imidazol-4-yl)propyl (S)-(-)-N-(1-phenylethyl)carbamate,
3-(1H-imidazol-4-yl)propyl N-cyclohexylcarbamate,
3-(1H-imidazol-4-yl)propyl N-phenylcarbamate,
3-(1H-Imidazol-4-yl )propyl N-methylphenyl)carbamate,
3-(1H-Imidazol-4-yl)propyl N-(4-trifluoromethyl)carbamate,
3-(1H-Imidazol-4-yl)propyl N-(3-trifluoromethylphenyl)carbamate,
3-(1H-Imidazol-4-yl)propyl N-(2-trifluoromethylphenyl)carbamate,
2-(1H-Imidazol-4-yl)propyl N-(2-phenylethyl)carbamate,
3-(1H-Imidazol-4-yl)propyl N-(4-nitrobenzyl)carbamate,
3-(1H-Imidazol-4-yl)propyl N-(4-aminobenzyl)carbamate,
3-(1H-Imidazol-4-yl)propyl N-(3-nitrophenyl)carbamate,
N-›2-(1H-Imidazol-4-yl)ethyl!-N-methyl-4-cyclohexylbutanamide,
3-Cyclohexylpropyl ester of 3-(1H-imidazol-4-yl)propanoic acid,
3-(1H-Imidazol-4-yl)propyl N-(2-nitrophenyl)carbamate,
3-(1H-Imidazol-4-yl)propyl N-(4-fluorophenyl)carbamate,
3-(1H-Imidazol-4-yl)propyl N-(2-phenylethyl)carbamate,
3-(1h-Imidazol-4-yl)propyl N-(4-fluorobenzyl)carbamate,
3-(1H-Imidazol-4-yl)propyl N-(4-chlorophenyl)carbamate,
3-(1H-Imidazol-4-yl)propyl N-(4-chlorobenzyl)carbamate,
3-(1H-Imidazol-4-yl)propyl N-(3-iodophenyl)carbamate,
3-(1H-Imidazol-4-yl)propyl N-(2-iodophenyl)carbamate,
3-(1H-Imidazol-4-yl)propyl N-(4-iodophenyl)carbamate,
3-(1H-Imidazol-4-yl)propyl N-(3-phenylpropyl)carbamate,
3-(1H-Imidazol-4-yl)propyl N-(4-trifluoromethylbenzyl)carbamate,
3-(1H-Imidazol-4-yl)propyl N-benzyl-N-methylcarbamate,
3-(1H-Imidazol-4-yl)propyl N-benzyl-N-isopropylcarbamate,
3-(4-Chlorophenyl)propyl 3-(1H-imidazol-4-yl)propyl ether,
(4-Chlorophenyl)methyl 3-(1H-imidazol-4-yl)propyl ether,
Cyclohexylmethyl (1H-imidazol-4-yl)methyl ether,
3-(4-Fluorophenyl)propyl 3-(1H-imidazol-4-yl)propyl ether,
p-Nitrophenyl trans-3-(1H-imidazol-4-yl)-2-propenoate,
2-{›2-(1H-Imidazol-4-yl)ethyl!amino}pyrimidine,
2-{›2-(1H-Imidazol-4-yl)ethyl!amino}benzothiazole,
2-{›2-(1H-Imidazol-4-yl)ethyl!amino}pyridine,
2-{›2-(1H-Imidazol-4-yl)ethyl!amino}-3-nitropyridine,
2-{›2-(1H-Imidazol-4-yl)ethyl!amino}-5-nitropyridine,
2-{›2-(1H-Imidazol-4-yl)ethyl!amino}thiazole,
2-{›2-(1H-Imidazol-4-yl)ethyl!amino}pyrazine,
2-{›2-(1H-Imidazol-4-yl)ethyl!amino}-3,6-dimethylpyrazine,
1-{›2-(1H-Imidazol-4-yl)ethyl!amino}-4-nitrobenzene,
2-{›2-(1H-Imidazol-4-yl)ethyl!amino}-5-trifluoromethylpyridine,
4-{›2-(1H-Imidazol-4-yl)ethyl!amino}-2-chloropyridine,
2-{›2-(1H-Imidazol-4-yl)ethyl!amino}-5-carbomethoxypyridine,
2-{›2-(1H-Imidazol-4-yl)ethyl!amino}-4-nitropyridine-N-oxide,
2-{›3-(1H-Imidazol-4-yl)propyl!amino}-5-nitropyridine,
2-{2-›(1H-Imidazol-4-yl)methylthio!ethylamino}-5-nitropyridine,
2-{›2-(1H-Imidazol-4-yl)ethyl!amino}-5-aminopyridine,
2-›(1H-Imidazol-4-yl)methylthio!-5-nitropyridine,
2-{2-›1H-Imidazol-4-yl!ethylthio}-5-nitropyridine,
2-{›2-(1H-Imidazol-4-yl)ethyl!thio}pyridine,
2-{›2-(1H-Imidazol-4-yl)ethyl!thio}-1H-imidazole,
4-›2-(4-Nitrophenoxy)ethyl!-1H-imidazole,
4-›2-(4-Carbomethoxyphenoxy)ethyl)!-1H-imidazole,
4-›2-(4-Cyanophenoxy)ethyl!-1H-imidazole,
4-›2-(4-Acetylphenoxy)ethyl!-1H-imidazole,
4-›2-(4-Ethoxycarbonylphenoxy)ethyl!-1H-imidazole,
4-›2-(3-Nitrophenoxy)ethyl!-1H-imidazole,
4-›2-(4-Methoxyphenoxy)ethyl!-1H-imidazole,
4-›2-(4-Propylphenoxy)ethyl!-1H-imidazole,
4-›2-(4-Bromophenoxy)ethyl!-1H-imidazole,
4-›2-(3,5-Dichlorophenoxy)ethyl!-1H-imidazole,
4-›2-(2,3,4,5,6-Pentafluorophenoxy)ethyl!-1H-imidazole,
4-›2-(4-Ethylphenoxy)ethyl!-1H-imidazole,
4-›2-(3-Cyanophenoxy)ethyl!-1H-imidazole,
4-›2-(2-Cyanophenoxy)ethyl!-1H-imidazole,
4-›2-(2-Naphthyloxy)ethyl!-1H-imidazole,
4-›2-(4-Trifluoromethylphenoxy)ethyl!-1H-midazole,
4-›2-(1-Naphthyloxy)ethyl!-1H-imidazole,
4-›2-(4-Benzoylphenoxy)ethyl!-1H-imidazole,
4-›2-(4-Nitrophenylthio)ethyl!-1H-imidazole,
4-›3-(4-Cyanophenoxy)propyl!-1H-imidazole,
4-›3-(4-Trifluoromethylphenoxy)propyl!-1H-imidazole, in the presence of presence or absence of a therapeutically acceptable vehicle or excipient.