Phenylalkyl diamine and amide analogs

1. A racemic or enantiomerically enriched phenylalkyldiamine compound represented by the structural formula (I):

wherein m is 1, n is 1, X and Y are independently selected from the group consisting of hydrogen, lower alkyl of 1 to 8 carbon atoms, halogen selected from F, Cl, Br and I, alkoxy containing 1 to 3 carbon atoms, nitro, hydroxy and trifluoromethyl; R 1 and R 2 are hydrogen, and Z is a radical derived from 5 to 7-membered aliphatic cyclic compounds selected from hexamethyleneimine, 4-benzylpiperidine, N-benzylpiperazine, substituted 4-benzoylpiperidine and their derivatives having the general formula (II) or (II′)

wherein X′ and Y′ are independently selected from the group consisting of hydrogen, lower alkyl of 1 to 8 carbon atoms, halogen selected from F, Cl, Br and I, alkoxy containing 1 to 3 carbon atoms, nitro, hydroxy, and trifluoromethyl; and the pharmaceutically acceptable salts thereof.

2. A racemic or enantiomerically enriched phenylalkyldiamine compound represented by the structural formula (I):

wherein m is 0, n is 2, X and Y are independently selected from the group consisting of hydrogen, lower alkyl of 1 to 8 carbon atoms, halogen selected from F, Cl, Br and I, alkoxy containing 1 to 3 carbon atoms, nitro, hydroxy and trifluoromethyl; R 1 and R 2 are hydrogen, and Z is a radical derived from 5 to 7-membered aliphatic cyclic compounds selected from morpholine, 4-benzylpiperidine, N-benzylpiperazine, substituted 4-benzoylpiperidine and their derivatives having the general formula (II) or (II′)

wherein X′ and Y′ are independently selected from the group consisting of hydrogen, lower alkyl of 1 to 8 carbon atoms, halogen selected from F, Cl, Br and I, alkoxy containing 1 to 3 carbon atoms, nitro, hydroxy, and trifluoromethyl; and the pharmaceutically acceptable salts thereof.

3. A racemic or enantiomerically enriched phenylalkylamino amide compounds represented by the structural formula (XI):

wherein m is 1, n is 1, l is 0–3, X and Y are independently selected from the group consisting of hydrogen, lower alkyl of 1 to 8 carbon atoms, halogen selected from F, Cl, Br and I, alkoxy containing 1 to 3 carbon atoms, nitro, hydroxy and trifluoromethyl; R3 are selected from the group consisting of hydrogen, phenyl and 3,4-dichlorophenyl; and_Z is a radical derived from 5 to 7-membered aliphatic cyclic compounds selected from pyrrolidine, piperidine, hexamethyleneimine, morpholine, 4-benzylpiperidine, N-benzylpiperazine, substituted 4-benzoylpiperidine and their derivatives having the general formula (II) or (II′)

wherein X′ and Y′ are independently selected from the group consisting of hydrogen, lower alkyl of 1 to 8 carbon atoms, halogen selected from F, Cl, Br and I, alkoxy containing 1 to 3 carbon atoms, nitro, hydroxy, and trifluoromethyl; and the pharmaceutically acceptable salts thereof.

4. A racemic or enantiomerically enriched phenylalkylamino amide compounds represented by the structural formula (XI):

wherein m is 0, n is 2, l is 0–3, X and Y are independently selected from the group consisting of hydrogen, lower alkyl of 1 to 8 carbon atoms, halogen selected from F, Cl, Br and I, alkoxy containing 1 to 3 carbon atoms, nitro, hydroxy and trifluoromethyl; R3 are selected from the group consisting of hydrogen, phenyl and 3,4-dichlorophenyl; and_Z is a radical derived from 5 to 7-membered aliphatic cyclic compounds selected from hexamethyleneimine, 4-benzylpiperidine, N-benzylpiperazine, substituted 4-benzoylpiperidine and their derivatives having the general formula (II) or (II′)

wherein X′ and Y′ are independently selected from the group consisting of hydrogen, lower alkyl of 1 to 8 carbon atoms, halogen selected from F, Cl, Br and I, alkoxy containing 1 to 3 carbon atoms, nitro, hydroxy, and trifluoromethyl; and the pharmaceutically acceptable salts thereof.

5. A racemic or enantiomerically enriched phenylalkylamino amide compounds represented by the structural formula (XVI):

wherein m is 1, n is 1 and l is 0–3; X and Y are independently selected from the group consisting of hydrogen, lower alkyl of 1 to 8 carbon atoms, halogen selected from F, Cl, Br and I, alkoxy containing 1 to 3 carbon atoms, nitro, hydroxy and trifluoromethyl; R3 are independently selected from the group consisting of hydrogen phenyl and 3,4-dichlorophenyl; and Z is a radical derived from 5 to 7-membered aliphatic cyclic compounds selected from hexamethyleneimine, 4-benzylpiperidine, N-benzylpiperazine, substituted 4-benzoylpiperidine and their derivatives having the general formula (III) or (II′)

wherein X′ and Y′ are independently selected from the group consisting of hydrogen, lower alkyl of 1 to 8 carbon atoms, halogen selected from F, Cl, Br and I, alkoxy containing 1 to 3 carbon atoms, nitro, hydroxy, and trifluoromethyl; and the pharmaceutically acceptable salts thereof.

6. A racemic or enantiomerically enriched phenylalkylamino amide compounds represented by the structural formula:

wherein m is 0, n is 2 and l is 0–3; X and Y are independently selected from the group consisting of hydrogen, lower alkyl of 1 to 8 carbon atoms, halogen selected from F, Cl, Br and I, alkoxy containing 1 to 3 carbon atoms, nitro, hydroxy and trifluoromethyl; R3 are independently selected from the group consisting of hydrogen, phenyl and 3,4-dichlorophenyl; and Z is a radical derived from 5 to 7-membered aliphatic cyclic compounds selected from hexamethyleneimine, 4-benzylpiperidine, N-benzylpiperazine, substituted 4-benzoylpiperidine and their derivatives having the general formula (II) or (II′)

wherein X′ and Y′ are independently selected from the group consisting of hydrogen, lower alkyl of 1 to 8 carbon atoms, halogen selected from F, Cl, Br and I, alkoxy containing 1 to 3 carbon atoms, nitro, hydroxy, and trifluoromethyl; and the pharmaceutically acceptable salts thereof.

7. A racemic or enantiomerically enriched phenylalkylamino sulfonamide compounds represented by the following structural formula (XIV):

wherein m is 0–2 and n is 1–4; X and Y are independently selected from the group consisting of hydrogen, lower alkyl of 1 to 8 carbon atoms, halogen selected from F, Cl, Br and I, alkoxy containing 1 to 3 carbon atoms, nitro, hydroxy and trifluoromethyl; R5 is selected from the group consisting of methyl, phenyl, 2-nitrophenyl, 4-methylphenyl, 2,4-dinitrophenyl, 3-nitrophenyl, 2,4,6-triisopropylphenyl and 2-thiophenyl; and Z is a radical derived from 5 to 7-membered aliphatic cyclic compounds selected from pyrrolidine, piperidine, hexamethyleneimine, morpholine, 4-benzylpiperidine, N-benzylpiperazine, substituted 4-benzoylpiperidine and their derivatives having the general formula (II) or (II′)

wherein X′ and Y′ are independently selected from the group consisting of hydrogen, lower alkyl of 1 to 8 carbon atoms, halogen selected from F, Cl, Br and I, alkoxy containing 1 to 3 carbon atoms, nitro, hydroxy and trifluoromethyl; and the pharmaceutically acceptable salts thereof.

8. A racemic or enantiomerically enriched phenylalkylamino sulfonamide compounds represented by the structural formula (XIV), in accordance with claim 7 , wherein m is 1, n is 1; R5 is selected from the group consisting of methyl, phenyl, 2-nitrophenyl, 4-methylphenyl, 2,4-dinitrophenyl, 3-nitrophenyl, 2,4,6-triisopropylphenyl and 2-thiophenyl; and Z is a radical derived from 5 to 7-membered aliphatic cyclic compounds selected from pyrrolidine, piperidine, hexamethyleneimine, morpholine, 4-benzylpiperidine, N-benzylpiperazine, substituted 4-benzoylpiperidine and their derivatives having the general formula (II) or (II′) and the pharmaceutically acceptable salts thereof.

9. A racemic or enantiomerically enriched phenylalkylamino sulfonamide compounds represented by the structural formula (XIV), in accordance with claim 7 , wherein m is 0, n is 2; R5 is selected from the group consisting of methyl, phenyl, 2-nitrophenyl, 4-methylphenyl, 2,4-dinitrophenyl, 3-nitrophenyl, 2,4,6-triisopropylphenyl and 2-thiophenyl; and Z is a radical derived from 5 to 7-membered aliphatic cyclic compounds selected from pyrrolidine, piperidine, hexamethyleneimine, morpholine, 4-benzylpiperidine, N-benzylpiperazine, substituted 4-benzoylpiperidine and their derivatives having the general formula (II) or (II′) and the pharmaceutically acceptable salts thereof.

10. A racemic or enantiomerically enriched phenylalkyldiamine compounds represented by the structural formula (XII):

wherein m is 1, n is 1 and l is 0–3; X and Y are independently selected from the group consisting of hydrogen, lower alkyl of 1 to 8 carbon atoms, halogen selected from F, Cl, Br and I, alkoxy containing 1 to 3 carbon atoms, nitro, hydroxy and trifluoromethyl; R3 are selected from the group consisting of hydrogen, phenyl and 3,4-dichlorophenyl; and Z is a radical derived from 5 to 7-membered aliphatic cyclic compounds selected from hexamethyleneimine, 4-benzylpiperidine, N-benzylpiperidine, substituted 4-benzoylpiperidine and their derivatives having the general formula (II) or (II′)

wherein X′ and Y′ are independently selected from the group consisting of hydrogen, lower alkyl of 1 to 8 carbon atoms, halogen selected from F, Cl, Br and I, alkoxy containing 1 to 3 carbon atoms, nitro, hydroxy and trifluoromethyl; and the pharmaceutically acceptable salts thereof.

11. A racemic or enantiomerically enriched phenylalkyldiamine compounds represented by the structural formula (XII):

wherein m is 0, n is 2 and l is 0–3; X and Y are independently selected from the group consisting of hydrogen, lower alkyl of 1 to 8 carbon atoms, halogen selected from F, Cl, Br and I, alkoxy containing 1 to 3 carbon atoms, nitro, hydroxy and trifluoromethyl; R3 are selected from the group consisting of hydrogen, phenyl and 3,4-dichlorophenyl; and_Z is a radical derived from 5 to 7-membered aliphatic cyclic compounds selected from hexamethyleneimine, 4-benzylpiperidine, N-benzylpiperazine, substituted 4-benzoylpiperidine and their derivatives having the general formula (II) or (III′)

wherein X′ and Y′ are independently selected from the group consisting of hydrogen, lower alkyl of 1 to 8 carbon atoms, halogen selected from F, Cl, Br and I, alkoxy containing 1 to 3 carbon atoms, nitro, hydroxy and trifluoromethyl; and the pharmaceutically acceptable salts thereof.

12. A racemic or enantiomerically enriched phenylalkyldiamine compounds represented by the following structural formula (XVII):

wherein m is 0–2, n is 1–4 and l is 0–3; X and Y are independently selected from the group consisting of hydrogen, lower alkyl of 1 to 8 carbon atoms, halogen selected from F, Cl, Br and I, alkoxy containing 1 to 3 carbon atoms, nitro, hydroxy, and trifluoromethyl; R3 are independently selected from the group consisting of hydrogen, phenyl and 3,4-dichlorophenyl; Z is a radical derived from 5 to 7-membered aliphatic cyclic compounds selected from hexamethyleneimine, 4-benzylpiperidine, N-benzylpiperazine, substituted 4-benzoylpiperidine and their derivatives having the general formula (II) or (II′)

wherein X′ and Y′ are independently selected from the group consisting of hydrogen, lower alkyl of 1 to 8 carbon atoms, halogen selected from F, Cl, Br and I, alkoxy containing 1 to 3 carbon atoms, nitro, hydroxy, and trifluoromethyl; and the pharmaceutically acceptable salts thereof.

13. A racemic or enantiomerically enriched phenylalkyldiamine compounds represented by the structural formula (XVII), in accordance with claim 12 , wherein m is 1, n is 1 and l is 0–3; R3 are independently selected from the group consisting of hydrogen, phenyl and 3,4-dichlorophenyl; Z is a radical derived from 5 to 7-membered aliphatic cyclic compounds selected from hexamethyleneimine, 4-benzylpiperidine, N-benzylpiperazine, substituted 4-benzoylpiperidine and their derivatives having the general formula (II) or (II′) and the pharmaceutically acceptable salts thereof.

14. A racemic or enantiomerically enriched phenylalkyldiamine compounds represented by the structural formula (XVII), in accordance with claim 12 , wherein m is 0, n is 2 and l is 0–3; R3 are independently selected from the group consisting of hydrogen, phenyl and 3,4-dichlorophenyl; Z is a radical derived from 5 to 7-membered aliphatic cyclic compounds selected from hexamethyleneimine, 4-benzylpiperidine, N-benzylpiperazine, substituted 4-benzoylpiperidine and their derivatives having the general formula (II) or (II′) and the pharmaceutically acceptable salts thereof.

15. A phenylalkyldiamine and amide compound selected from the group consisting of:

d-1-benzyl-2-(1-hexamethyleneimino)ethylamine dihydrochloride;

l-1-benzyl-2-(N-succinimidyl)ethylamine hydrochloride;

1-(3-chlorobenzyl)-2-(1-hexamethyleneimino)ethylamine dihydrochloride;

1-[4-(tert-butyl)benzyl]-2-(1-hexamethyleneimino)ethylamine dihydrochloride;

1-[4-(trifluoromethyl)benzyl]-2-(1-hexamethyleneimino)ethylamine dihydrochloride;

1-(4-chlorobenzyl)-2-(1-hexamethyleneimino)ethylamine dihydrochloride;

1-(3,4-dichlorobenzyl)-2-(1-hexamethyleneimino)ethylamine dihydrochloride;

1-[3-(trifluoromethyl)benzyl]-2-(1-hexamethyleneimino)ethylamine dihydrochloride;

1-(2,6-dichlorobenzyl)-2-(1-hexamethyleneimino)ethylamine dihydrochloride;

1-(2-methylbenzyl)-2-(1-hexamethyleneimino)ethylamine dihydrochloride;

1-(2,4-dichlorobenzyl)-2-(1-hexamethyleneimino)ethylamine dihydrochloride;

1-(phenethyl)-2-(1-hexamethyleneimino)ethylamine dihydrochloride;

1-(3,4-dichlorobenzyl)-2-[1-(4-benzylpiperidinyl)]ethylamine dihydrochloride;

1-[4-(tert-butyl)benzyl]-2-[1-(4-benzylpiperidinyl)]ethylamine dihydrochloride;

1-(2,4-dichlorobenzyl)-2-[1-(4-benzylpiperidinyl)]ethylamine dihydrochloride;

1-(4-chlorobenzyl)-2-[1-(4-benzoylpiperidinyl)]ethylamine;

1-[4-(tert-butyl)benzyl]-3-[1-(4-benzoylpiperidinyl)]propylamine;

1-[4-(tert-butyl)benzyl]-3-[1-(4-(phenylacetyl)]piperidinyl)]propylamine;

1-[4-(tert-butyl)benzyl]-3-[1-(4-benzylpiperidinyl)]propylamine;

d-1-benzyl-2-[1-(4-benzoylpiperidinyl)]ethylamine;

1-benzyl-2-[1-(4-benzoylpiperidinyl)]ethylamine;

l-1-benzyl-2-[1-(4-benzoylpiperidinyl)]ethylamine;

l-1-benzyl-2-[1-(4-(phenylacetyl)piperidinyl)]ethylamine;

l-1-benzyl-2-[1-(4-(4-chlorobenzoyl)piperidinyl)]ethylamine;

l-1-benzyl-2-[1-(4-(4-fluorobenzoyl)piperidinyl)]ethylamine;

l-1-benzyl-2-[1-(4-(3,4-dichlorobenzoyl)piperidinyl)]ethylamine;

1-(3,4-dichlorobenzyl)-2-[1-(4-benzoylpiperidinyl)]ethylamine;

1-(4-chlorobenzyl)-2-[1-(4-(3,4-dichlorobenzoyl)piperidinyl)]ethylamine;

1-(3,4-dichlorobenzyl)-2-[1-(4-(3,4-dichlorobenzoyl)piperidinyl)]ethylamine;

l-1-benzyl-2-[1-(4-(4-methoxybenzoyl)piperidinyl)]ethylamine;

1-(4-chlorobenzyl)-2-[1-(4-(4-methoxybenzoyl)piperidinyl)]ethylamine;

l-1-benzyl-2-[1-(4-(4-tert-butylbenzoyl)piperidinyl)]ethylamine;

1-[4-(tert-butyl)benzyl]-2-[1-(4-benzoylpiperidinyl)]ethylamine;

1-phenyl-3-[1-(4-benzylpiperidinyl)]-n-propylamine dihydrochloride;

1-phenyl-3-[1-(3-methylpiperidinyl)]-n-propylamine;

1-phenyl-3-[1-(4-benzoylpiperidinyl)]-n-propylamine dihydrochloride;

1-phenyl-3-[1-(1,2,3,4-tetrahydroisoquinolinyl)]-n-propylamine;

1-phenyl-3-[1-(4-(4-fluorobenzoyl)piperidinyl)]-n-propylamine;

1-phenyl-3-[1-(4-(phenylacetyl)piperidinyl)]-n-propylamine;

[1-(3-amino-3-phenyl-propyl)-piperidin-4-yl]-phenyl-methanol;

[1-(3-amino-3-phenyl-propyl)-piperidin-4-yl]-(4-fluoro-phenyl)-methanol;

N-benzoyl-1-(3,4-dichlorobenzyl)-2-(1-hexamethyleneimino)ethylamine;

d-N-(2-nitrobenzenesulfonyl)-1-benzyl-2-(1-pyrrolidinyl)ethylamine hydrochloride;

N-methyl-N-[2-(3,4-dichlorophenyl)acetyl]-1-[4-(tert-butyl)benzyl]-2-(1-hexamethyleneimino)ethylamine;

N-benzoyl-1-(3,4-dichlorobenzyl)-2-[1-(4-benzylpiperidinyl)]ethylamine;

N-[2-(3,4-dichlorophenyl)acetyl]-1-(3,4-dichlorobenzyl)-2-[1-(4-benzylpiperidinyl)]ethylamine;

N-[2-(3,4-Dichlorophenyl)acetyl]-1-(3,4-dichlorobenzyl)-2-(1-hexamethyleneimino)ethylamine;

N-benzoyl-1-(2,4-dichlorobenzyl)-2-[1-(4-benzylpiperidinyl)]ethylamine;

N-[2-(3,4-dichlorophenyl)acetyl]-1-(2,4-dichlorobenzyl]-2-[1-(4-benzylpiperidinyl)]ethylamine;

N-[2-(3,4-dichlorophenyl)acetyl]-1-phenyl-3-(1-hexamethyleneimino)-n-propylamine;

N-(p-toluenesulfonyl)-1-phenyl-3-(1-hexamethyleneimino)-n-propylamine;

N-benzoyl-1-phenyl-3-(1-hexamethyleneimino)-n-propylamine;

N-[2-(3,4-dichlorophenyl)acetyl]-1-phenyl-3-[1-(4-benzylpiperidinyl)]-n-propylamine;

N-[2-(3,4-dichlorophenyl)acetyl]-1-phenyl-3-[1-(4-(4-fluorobenzoylpiperidinyl))-n-propylamine;

N-(p-toluenesulfonyl)-1-phenyl-3-[1-(4-benzylpiperidinyl)]-n-propylamine;

N-(benzenesulfonyl)-1-phenyl-3-[1-(4-benzylpiperidinyl)]-n-propylamine;

N-(2,4-dinitrobenzenesulfonyl)-1-phenyl-3-[1-(4-benzylpiperidinyl)]-n-propylamine;

N-(methanesulfonyl)-1-phenyl-3-[1-(4-benzylpiperidinyl)]-n-propylamine;

N-(3-nitrobenzenesulfonyl)-1-phenyl-3-[1-(4-benzylpiperidinyl)]-n-propylamine;

N-(2-nitrobenzenesulfonyl)-1-phenyl-3-[1-(4-benzylpiperidinyl)]-n-propylamine;

N-(2,4,6-triisopropylbenzenesulfonyl)-1-phenyl-3-[1-(4-benzylpiperidinyl)]-n-propylamine;

N-benzoyl-1-phenyl-3-[1-(4-benzylpiperidinyl) ]-n-propylamine;

N-(2-thiophenesulfonyl)-1-phenyl-3-[1-(4-benzylpiperidinyl)]-n-propylamine;

N-(2-nitrobenzenesulfonyl)-1-phenyl-3-[1-(4-benzoylpiperidinyl)]-n-propylamine;

N-(2-nitrobenzenesulfonyl)-1-phenyl-3-[1-(4-(4-fluorobenzoyl)piperidinyl)]-n-propylamine;

N-(2-thiophenesulfonyl)-1-phenyl-3-[1-(1,2,3,4-tetrahydroisoquinolinyl)]-n-propylamine;

N-benzoyl-1-phenyl-3-[1-(4-benzoylpiperidinyl)]-n-propylamine;

N-[2-(3,4-Dichlorophenyl)acetyl]-1-phenyl-3-[1-(4-benzoylpiperidinyl)]-n-propylamine;

N-benzenesulfonyl-1-phenyl-3-[1-(4-benzoylpiperidinyl)]-n-propylamine;

N-acetyl-1-phenyl-3-[1-(4-benzylpiperidinyl)]-n-propylamine;

N-benzyl-1-(3,4-dichlorobenzyl)-2-(1-hexamethyleneimino)ethylamine;

N-benzyl-1-[4-(tert-butyl)benzyl]-2-(1-hexamethyleneimino)ethylamine;

N-benzyl-1-(3,4-dichlorobenzyl)-2-[1-(4-benzylpiperidinyl)]ethylamine;

N-(3,4-dichlorophenethyl-1-(3,4-dichlorobenzyl)-2-(1-hexamethyleneimino)ethylamine;

N-(3,4-dichlorophenethyl)-1-phenyl-3-(1-hexamethyleneimino)-n-propylamine;

N-(3,4-dichlorophenethyl)-1-phenyl-3-[1-(4-benzylpiperidinyl)]-n-propylamine;

N-formyl-1-(3,4-dichlorobenzyl)-2-(1-hexamethyleneimino)ethylamine;

N-formyl-1-(3,4-dichlorobenzyl)-2-[1-(4-benzylpiperidinyl)]ethylamine;

N-formyl-1-[4-(tert-butyl)benzyl]-2-[1-(4-benzylpiperidinyl)]ethylamine;

N-formyl-1-(2,4-dichlorobenzyl)-2-[1-(4-benzylpiperidinyl)]ethylamine;

N-formyl-1-phenyl-3-[1-(4-benzylpiperidinyl)]-n-propylamine;

N-(3,4-dichlorophenethyl)-N-formyl-1-phenyl-3-[1-(4-benzylpiperidinyl)]-n-propylamine;

N-formyl-N-methyl-1-phenyl-3-[1-(4-benzylpiperidinyl)]-n-propylamine;

N-formyl-1-phenyl-3-[1-(4-benzoylpiperidinyl)]-n-propylamine;

N-{3-[4-(hydroxy-phenyl-methyl)-piperidin-1-yl]-1-phenyl-propyl}-formamide;

N-methyl-1-[4-(tert-butyl)benzyl]-2-(1-hexamethyleneimino)ethylamine;

N,N-dimethyl-1-[4-(tert-butyl)benzyl]-2-(1-hexamethyleneimino)ethylamine;

N-methyl-1-(3,4-dichlorobenzyl)-2-[1-(4-benzylpiperidinyl)]ethylamine;

N-methyl-1-[4-(tert-butyl)benzyl]-2-[1-(4-benzylpiperidinyl)]ethylamine dihydrochloride;

N-methyl-1-(2,4-dichlorobenzyl)-2-[1-(4-benzylpiperidinyl)]ethylamine;

N-methyl-1-phenyl-3-[1-(4-benzylpiperidinyl)]-n-propylamine;

N-methyl-1-phenyl-3-(1-hexamethyleneimino)-n-propylamine;

N,N-dimethyl-1-phenyl-3-[1-(4-benzylpiperidinyl)]-n-propylamine; and

N-methyl-1-phenyl-3-[1-(4-(4-fluorobenzoyl)piperidinyl)]-n-propylamine.