NOVEL SUBSTITUTED ARYL DERIVATIVES, THEIR PROCESS OF PREPARATION AND THEIR THERAPEUTICAL USES AS ANTI-HIV AGENTS

• US 20120022054A1
• Filed: 12/10/2009
• Published: 01/26/2012
• Est. Priority Date: 12/10/2008
• Status: Abandoned Application

• Current Assignee: Institut National De La Sante Et De La Recherche Medicale (Inserm) (Allianz Global Investors GmbH), Centre National De La Recherche Scientifique, Laboratoire Biodim (Eurolord Trading SARL)
• Original Assignee: Laboratoire Biodim (Eurolord Trading SARL)
• Inventors: Benarous, Richard, Paris, Jean-Marc, Emiliani, Stephane, Barbey-Treve, Sabine, Berrut, Sebastien, Berlioz-Torrent, Clarisse
• Application Number:
  US13/139,259
• Publication Number:
  US 20120022054A1
• Time in Patent Office: Days
• US Class Current: 514/229.2
• CPC Class Codes: A61P 31/14 for RNA viruses
• CPC Class Codes: A61P 31/18 for HIV
• CPC Class Codes: C07C 233/22 having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
• CPC Class Codes: C07C 235/20 having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
• CPC Class Codes: C07C 235/34 having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
• CPC Class Codes: C07C 235/74 of a saturated carbon skeleton
• CPC Class Codes: C07C 237/06 having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
• CPC Class Codes: C07C 237/08 having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
• CPC Class Codes: C07C 2601/02 with a three-membered ring
• CPC Class Codes: C07C 317/44 having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
• CPC Class Codes: C07C 323/60 with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
• CPC Class Codes: C07C 327/42 to hydrogen atoms or to carbon atoms of a saturated carbon skeleton
• CPC Class Codes: C07D 213/40 Acylated substituent nitrogen atom
• CPC Class Codes: C07D 233/06 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
• CPC Class Codes: C07D 239/78 with hetero atoms directly attached in position 2
• CPC Class Codes: C07D 295/135 with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
• CPC Class Codes: C07D 307/77 ortho- or peri-condensed with carbocyclic rings or ring systems
• CPC Class Codes: C07D 471/04 Ortho-condensed systems

Abstract

The present invention concerns novel substituted aryl derivatives, their process of preparation and their use for inhibiting virus replication and for treating viral diseases or disorders such as HIV and/or HCV infection.

Claims

1. Compounds of formula (I):

2. Compounds of formula (I) according to claim 1, wherein X represents a group chosen from —

U—

, —

CRR′

—

, —

NT-, —

O—

, —

S(O)_q—

, —

C(═

O)—

, where the R of —

NR—

may be optionally linked with a R7 to form with the N atom to which it is attached a N-containing heterocycle fused with said

3. Compounds of formula (I) according to claim 1, wherein:

R4 represents an aryl or heteroaryl said aryl or heteroaryl group being optionally fused with an aryl, heteroaryl, saturated or unsaturated cycloalkyl or heterocyclic ring and said optionally fused aryl or heteroaryl being optionally substituted by one or more substituent(s) chosen from;

-halogen atom;

-Alkyl;

-Aryl;

—

OAryl;

-Alkyl-OR;

-Heterocycle optionally substituted by an -Alkyl, -AlkylOR, -AlkylNRR′

, -Alkylaryl, —

OR, -Alkyl-Heterocycle, —

C(═

O)Alkyl or —

C(═

O)OAlkyl group;

-Alkylaryl;

-Alkyl-Heterocycle;

—

CN;

—

NO₂;

perfluoroalkyl-;

perfluoroalkoxy-;

polyfluoroalkyl-;

polyfluoroalkoxy-;

—

OHeterocycle-Alkyl;

—

OR;

—

NRR′

;

═

O;

—

C(═

O)R;

—

C(═

O)NRR′

;

—

O-Alkyl-C(═

O)NRR′

, —

OAlkyl-NRR′

, —

NR—

C(═

O)R′

;

—

C(═

O)OR;

—

S(O)R—

S(O)₂R;

—

OC(═

O)R;

4. Compounds of formula (I) according to claim 1, wherein R1 is O.

5. Compounds according to claim 1, wherein R3 represents a H atom or a group chosen from -alkyl, -aryl.

6. Compounds according to claim 1, wherein R4 represents an aryl optionally fused with an aryl, heteroaryl, or saturated heterocyclic ring and said optionally fused aryl being optionally substituted by one or more substituent(s) chosen from:

-halogen atom;

-Alkyl;

-Aryl;

—

OAryl;

-Alkyl-OR;

-Heterocycle optionally substituted by an -Alkyl, -AlkylOR, -AlkylNRR′

, -Alkylaryl, —

OR, -Alkyl-Heterocycle, —

C(═

O)Alkyl or —

C(═

O)OAlkyl group;

-Alkylaryl;

-Alkyl-Heterocycle;

perfluoroalkyl-;

polyfluoroalkyl-;

polyfluoroalkoxy-;

—

OHeterocycle-Alkyl;

—

OR;

—

O-Alkyl-C(═

O)NRR′

, —

OAlkyl-NRR′

, —

NR—

C(═

O)R′

;

—

C(═

O)OR;

—

OC(═

O)R.

7. Compounds according to claim 1, wherein R5 represents a group -Alkyl, -Alkyl-OR, or -Cycloalkyl, each being optionally substituted by one or more substituents chosen from -polyfluoroalkyl groups or, when p is 0, R5 may additionally represent an alkylene or alkenylene chain comprising 2 to 4 atoms, including C, N, O, so that R5 is linked to a ring member of R4 so as to form together with the N atom to which they are attached a N-containing heterocycle or heteroaryl optionally comprising one or more further heteroatom and optionally substituted by a group chosen from halogen atom, -alkyl, -aryl, -alkylaryl, —

CN, —

NO₂, perfluoroalkyl-, perfluoroalkoxy-, polyfluoroalkyl-, polyfluoroalkoxy-, —

OR, —

NRR′

, ═

O, —

C(═

O)R, —

C(═

O)NRR′

, —

C(═

O)OR, —

S(O)_qR, —

OC(═

O)R.

8. Compounds according to claim 1, wherein R6 represents a H atom or a group chosen from —

C(═

O)NRR′

, —

C(═

O)OR.

9. Compounds according to claim 1, wherein R7, identical or different is independently chosen from Halogen atoms;

—

OR;

—

O—

C(═

O)R;

—

NR—

C(═

O)R′

;

—

NR—

S(O)_q—

R′

;

perfluoroalkyl;

—

C(═

O)OR;

—

C(═

O)Alkyl;

—

C(═

O)Aryl;

heteroaryl;

—

C(═

O)—

NRR′

;

—

OAlkylAryl;

polyfluoroalkyl-;

or 2 R7 form together with the atoms to which they are attached an unsubstituted ring chosen from aryl, heteroaryl, or unsaturated heterocyclic ring fused with

10. Compounds according to claim 1, wherein X represents a group chosen from —

U—

, —

CRR′

—

, —

NT-, —

S—

, —

S(O)—

, —

C(═

O)—

, —

S(O)₂—

11. Compounds according to claim 1, wherein Y represents a hydrogen atom.

12. Compounds according to claim 1, wherein

13. Compounds according to claim 1, wherein m is 1 or 2.

14. Compounds according to claim 1, wherein n is 2.

15. Compounds according to claim 1, wherein p is 1.

16. Compounds according to claim 1, wherein:

R1 is O;

R3 represents a H atom;

R4 represents an aryl, preferably phenyl, or heteroaryl, preferably pyridyl, optionally fused with an aryl such as phenyl, or heteroaryl such as pyridyle, and said optionally fused aryl or heteroaryl being optionally substituted by one or more identical or different substituent(s) chosen from;

-halogen atom;

-Alkyl;

-heterocycle;

OH;

Oalkyl;

R5 represent a group -Alkyl;

R6 represents a H atom;

each R7, identical or different is independently chosen from Halogen atoms;

—

OR;

—

CN;

X represents a group chosen from —

NT-, —

S(O)_q—

, —

C(═

O)—

, —

U—

, where T represent a C2or C3 alkylene or alkenylene chain linked with a member of

17. A compound of formula (I) according to claim 1 chosen from the group consisting in:

N-benzyl-4-[(4-hydroxyphenyl)thio]-N-methylbutanamide

N,N-dibenzyl-4-[(4-hydroxyphenyl)thio]butanamide

4-[(4-hydroxyphenyl)thio]-N-methyl-N-(pyridin-3-ylmethyl)butanamide

N-ethyl-4-[(4-hydroxyphenyl)thio]-N-(pyridin-4-ylmethyl)butanamide

N-benzyl-4-(4-methoxyphenoxy)-N-methylbutanamide

4-(4-methoxyphenoxy)-N-methyl-N-(pyridin-3-ylmethyl)butanamide

N-benzyl-4-[(3-hydroxyphenyl)thio]-N-methylbutanamide

4-[(3-hydroxyphenyl)thio]-N-methyl-N-(pyridin-3-ylmethyl)butanamide

N-benzyl-4-[(4-methoxyphenyl)thio]-N-methylbutanamide

N,N-dibenzyl-4-[(4-methoxyphenyl)thio]butanamide

4-[(4-methoxyphenyl)thio]-N-methyl-N-(pyridin-3-ylmethyl)butanamide

N,N-dibenzyl-4-[(3-hydroxyphenyl)thio]butanamide

N,N-dibenzyl-4-(4-methoxyphenoxy)butanamide

N-benzyl-4-(4-benzyloxyphenoxy)-N-methylbutanamide

4-[(4-hydroxyphenyl)thio]-N-methyl-N-[1-phenylethyl]butanamide

N-(4-chlorobenzyl)-4-[(4-hydroxyphenyl)thio]-N-methylbutanamide

N-(2-chlorobenzyl)-4-[(4-hydroxyphenyl)thio]-N-methylbutanamide

N-(4-fluorobenzyl)-4-[(4-hydroxyphenyl)thio]-N-methylbutanamide

4-[(4-hydroxyphenyl)thio]-N-(4-methoxybenzyl)-N-methylbutanamide

4-[(4-hydroxyphenyl)thio]-N-methyl-N-[4-(trifluoromethyl)benzyl]butanamide

4-[(4-hydroxyphenyl)thio]-N-methyl-N-(4-methylbenzyl)butanamide

N-benzyl-4-(4-hydroxyphenoxy)-N-methylbutanamide

N-(3-chlorobenzyl)-4-[(4-hydroxyphenyl)thio]-N-methylbutanamide

4-[(4-hydroxyphenyl)thio]-N-methyl-N-phenylbutanamide

N-benzhydryl-4-[(4-hydroxyphenyl)thio]-N-methylbutanamide

4-{[4-oxo-4-(2-phenyl-4,5-dihydro-1H-imidazol-1-yl)butyl]thio}phenol

4-[(4-hydroxyphenyl)thio]-N,N-bis(pyridin-2-ylmethyl)butanamide

4-[(4-hydroxyphenyl)thio]-N-methyl-N-(2-methylbenzyl)butanamide

N-(2,4-dichlorobenzyl)-4-[(4-hydroxyphenyl)thio]-N-methylbutanamide

4-[(4-hydroxyphenyl)thio]-N-(2-methoxybenzyl)-N-methylbutanamide

N-(2,3-dichlorobenzyl)-4-[(4-hydroxyphenyl)thio]-N-methylbutanamide

N-(2-fluorobenzyl)-4-[(4-hydroxyphenyl)thio]-N-methylbutanamide

N-(2,6-dichlorobenzyl)-4-[(4-hydroxyphenyl)thio]-N-methylbutanamide

N-(2-chlorobenzyl)-4-[(4-hydroxyphenyl)sulfinyl]-N-methylbutanamide

N-(2-chloro-6-fluorobenzyl)-4-[(4-hydroxyphenyl)thio]-N-methylbutanamide

N-(2-ethoxybenzyl)-4-[(4-hydroxyphenyl)thio]-N-methylbutanamide

N-(2,3-dimethoxybenzyl)-4-[(4-hydroxyphenyl)thio]-N-methylbutanamide

N-(2-furylmethyl)-4-[(4-hydroxyphenyl)thio]-N-methylbutanamide

4-[(4-hydroxyphenyl)thio]-N-methyl-N-[2-(trifluoromethoxy)benzyl]butanamide

4-[(3-hydroxyphenyl)thio]-N-(2-methoxybenzyl)-N-methylbutanamide

4-[(4-fluorophenyl)thio]-N-(2-methoxybenzyl)-N-methylbutanamide

4-[(4-hydroxyphenyl)thio]-N-methyl-N-(pyridin-2-ylmethyl)butanamide

N-(2-hydroxybenzyl)-4-[(4-hydroxyphenyl)thio]-N-methylbutanamide

N-(2,3-dihydro-1-benzofuran-7-ylmethyl)-4-[(4-hydroxyphenyl)thio]-N-methylbutanamide

4-[(2-hydroxyphenyl)thio]-N-(2-methoxybenzyl)-N-methylbutanamide

4-{[4-(acetylamino)phenyl]thio}-N-(2-methoxybenzyl)-N-methylbutanamide

5-(4-hydroxyphenyl)-N-(2-methoxybenzyl)-N-methylpentanamide

N-(2-methoxybenzyl)-N-methyl-4-{[4-(methylsulfonylamino)phenyl]thio}butanamide

N-[2-(acetylamino)benzyl]-4-[(4-hydroxyphenyl)thio]-N-methylbutanamide

4-[(4-hydroxyphenyl)thio]-N-methyl-N-(1-naphthylmethyl)butanamide

N-(2-methoxybenzyl)-N-methyl-4-(2-naphthylthio)butanamide

N-(2-methoxybenzyl)-N-methyl-4-{[4-(trifluoromethyl)phenyl]thio}butanamide

N-(2-methoxybenzyl)-N-methyl-4-(quinolin-2-ylthio)butanamide

N-(1,3-benzodioxol-4-ylmethyl)-4-[(4-hydroxyphenyl)thio]-N-methylbutanamide

N-(2-methoxybenzyl)-N-methyl-4-{[5-(trifluoromethyl)pyridin-2-yl]thio}butanamide

4-[(4-hydroxyphenyl)thio]-N-methyl-N-[2-(trifluoromethyl)benzyl]butanamide

4-[(4-hydroxyphenyl)thio]-N-(2-isopropoxybenzyl)-N-methylbutanamide

N-(2-methoxybenzyl)-4-[(4-methoxyphenyl)thio]-N-methylbutanamide

4-[(5-chloropyridin-2-yl)thio]-N-(2-methoxybenzyl)-N-methylbutanamide

N-(2-chlorobenzyl)-4-[(4-fluorophenyl)thio]-N-methylbutanamide

Methyl 4-({4-[(2-methoxybenzyl)methylamino]-4-oxobutyl}thio)benzoate

N-(2-methoxybenzyl)-N-methyl-4-(quinoxalin-2-ylthio)butanamide

4-[(4-fluorophenyl)thio]-N-(2-hydroxybenzyl)-N-methylbutanamide

4-[(4-hydroxyphenyl)thio]-N-methyl-N-[2-(4-methylpiperazin-1-yl)benzyl]butanamide

4-({4-[(2-methoxybenzyl)(methyl)amino]-4-oxobutyl}thio)benzoic acid

4-[(4-fluorophenyl)thio]-N-(2-methoxyphenyl)-N-methylbutanamide

4-({4-[(2-methoxybenzyl)(methyl)amino]-4-oxobutyl}thio)-N-methylbenzamide

4-[(4-fluorophenyl)(methyl)amino]-N-(2-methoxybenzyl)-N-methylbutanamide

4-[(4-hydroxyphenyl)thio]-N-methyl-N-(2-morpholin-4-ylbenzyl)butanamide

5-[(4-hydroxyphenyl)thio]-N-(2-methoxybenzyl)-N-methylpentanamide

4-[(4-fluorophenyl)thio]-N-[2-(2-methylamino-2-oxoethoxy)benzyl]-N-methylbutanamide

N-[2-(2-aminoethoxy)benzyl]-4-[(4-fluorophenyl)thio]-N-methylbutanamide

4-(1H-indol-5-yloxy)-N-(2-methoxybenzyl)-N-methylbutanamide

N-(2,3-dichlorobenzyl)-4-[(4-fluorophenyl)thio]-N-methylbutanamide

N-{2-[2-(dimethylamino)ethoxy]benzyl}-4-[(4-fluorophenyl)thio]-N-methylbutanamide

Methyl 2-{[{4-[(4-hydroxyphenyl)thio]butanoyl}(methyl)amino]-methyl}benzoate 2-{[{4-[(4-hydroxyphenyl)thio]butanoyl}(methyl)amino]methyl}benzoic acid

Ethyl 4-[2-({4-[(4-hydroxyphenyl)thio]butanoyl}methylamino)methylphenyl]piperazine-1-carboxylate

4-[(4-hydroxyphenyl)thio]-N-[2-(4-hydroxypiperidin-1-yl)benzyl]-N-methylbutanamide

4-[(4-hydroxyphenyl)thio]-N-methyl-N-(2-phenoxybenzyl)butanamide

4-[(4-hydroxyphenyl)thio]-N-methyl-N-(2-piperazin-1-ylbenzyl)butanamide

4-[(4-fluorophenyl)thio]-N-(2-isopropoxybenzyl)-N-methylbutanamide

4-[(4-fluorophenyl)thio]-N-methyl-N-(2-morpholin-4-ylbenzyl)butanamide

Methyl-4-[(4-hydroxyphenyl)thio]-2-{[(2-methoxybenzyl)(methyl)amino]-carbonyl}butanoate

4-[(4-hydroxyphenyl)thio]-N-methyl-N-(2-benzylbenzyl)butanamide

4-[(4-hydroxyphenyl)thio]-N-methyl-N-{2-[4-(2-morpholin-4-ylethyl)piperazin-1-yl]benzyl}butanamide

N-[2-(4-acetylpiperazin-1-yl)benzyl]-4-({4-[benzyl(methyl)amino]-4-oxobutyl}thio)phenyl acetate

4-[(4-hydroxyphenyl)thio]-2-{[(2-methoxybenzyl)(methyl)amino]carbonyl}butanoic acid

N-[2-(4-benzylpiperazin-1-yl)benzyl]-4-[(4-hydroxyphenyl)thio]-N-methylbutanamide

5-(4-hydroxyphenyl)-N-methyl-N-(2-morpholin-4-ylbenzyl)pentanamide

5-(4-fluorophenyl)-N-(2-methoxybenzyl)-N-methyl-5-oxopentanamide

N-(1,1′

-biphenyl-2-ylmethyl)-4-[(4-hydroxyphenyl)thio]-N-methylbutanamide

4-[(4-hydroxyphenyl)thio]-N-(2-methoxybenzyl)-N-methylbutanethioamide

5-(4-fluorophenyl)-N-(2-methoxybenzyl)-N-methylpentanamide

N-[2-(4-acetylpiperazin-1-yl)benzyl]-4-[(4-hydroxyphenyl)thio]-N-methylbutanamide

4-[(3,4-difluorophenyl)thio]-N-(2-methoxybenzyl)-N-methylbutanamide

4-[(3-fluorophenyl)thio]-N-(2-methoxybenzyl)-N-methylbutanamide

2-{2-[(4-hydroxyphenyl)thio]ethyl}-N-(2-methoxybenzyl)-N,N′

-dimethylmalonamide

5-(4-hydroxyphenyl)-N-(2-isopropoxybenzyl)-N-methylpentanamide

N-(2-hydroxyethyl)-4-[(4-hydroxyphenyl)thio]-N-(2-methoxybenzyl)butanamide

4-[(4-fluorophenyl)methylamino]-N-(2-isopropoxybenzyl)-N-methylbutanamide

4-[(4-fluorophenyl)(methyl)amino]-N-methyl-N-[2-(trifluoromethyl)benzyl]butanamide

4-[(2,4-difluorophenyl)thio]-N-(2-methoxybenzyl)-N-methylbutanamide

N-{2-[4-(2-dimethylaminoethyl)piperazin-1-yl]benzyl}-4-[(4-hydroxyphenyl)thio]-N-methylbutanamide

4-[(4-hydroxyphenyl)thio]-N-(2-methoxybenzyl)-N-(2-morpholin-4-ylethyl)butanamide

4-[(4-hydroxyphenyl)thio]-N-[2-(methoxymethyl)benzyl]-N-methylbutanamide

N-cyclopropylmethyl-4-[(4-hydroxyphenyl)thio]-N-(2-methoxybenzyl)butanamide

N-ethyl-4-[(4-hydroxyphenyl)thio]-N-(2-methoxybenzyl)butanamide

N-(3-fluoro-2-methoxybenzyl)-4-[(4-hydroxyphenyl)thio]-N-methylbutanamide

4-[(4-hydroxyphenyl)thio]-N-(2-methoxy-3-methylbenzyl)-N-methylbutanamide

N-(5-chloro-2-methoxybenzyl)-4-[(4-hydroxyphenyl)thio]-N-methylbutanamide

4-[(3-chloro-4-fluorophenyl)thio]-N-(2-methoxybenzyl)-N-methylbutanamide

4-[(2-chloro-4-fluorophenyl)thio]-N-(2-methoxybenzyl)-N-methylbutanamide

N-(5-fluoro-2-methoxybenzyl)-4-[(4-hydroxyphenyl)thio]-N-methylbutanamide

4-[(4-hydroxyphenyl)thio]-N-methyl-N-[2-(morpholin-4-ylmethyl)benzyl]butanamide

N-{2-[4-(2-hydroxyethyl)piperazin-1-yl]benzyl}-4-[(4-hydroxyphenyl)thio]-N-methylbutanamide

N-(3,5-dichloro-2-methoxybenzyl)-4-[(4-hydroxyphenyl)thio]-N-methylbutanamide

4-[(4-hydroxyphenyl)thio]-N-(2-methoxy-4-methylbenzyl)-N-methylbutanamide

4-[(4-fluorophenyl)thio]-N-(2-methoxybenzyl)-N-(2,2,2-trifluoroethyl)butanamide

(3S)-4-[(4-fluorophenyl)thio]-3-hydroxy-N-(2-methoxybenzyl)-N-methylbutanamide

Methyl 4-({4-[methyl-(2-trifluoromethylbenzyl)amino]-4-oxobutyl}thio)benzoate

N-cyclopropyl-4-[(4-hydroxyphenyl)thio]-N-(2-methoxybenzyl)butanamide

4-[(4-{methyl [2-(trifluoromethyl)benzyl]amino}-4-oxobutyl)thio]benzoic acid

Methyl 5-fluoro-2-({4-[methyl-(2-methoxybenzyl)amino]-4-oxobutyl}thio)benzoate

4-[(4-fluorophenyl)methylamino]-N-[2-(4-methylpiperazin-1-yl)benzyl]-N-methylbutanamide

4-[(4-hydroxyphenyl)thio]-N-methyl-N-{2-[(1-methylpiperidin-4-yl)oxy]benzyl}butanamide

5-fluoro-2-({4-[(2-methoxybenzyl)(methyl)amino]-4-oxobutyl}thio)benzoic acid

4-[(4-hydroxyphenyl)thio]-N-methyl-N-[2-(1,2,3,6-tetrahydropyridin-4-yl)benzyl]butanamide

4-[(4-fluorophenyl)sulfonyl]-N-(2-methoxybenzyl)-N-methylbutanamide

4-[(4-fluorophenyl)(2-hydroxyethyl)amino]-N-(2-methoxybenzyl)-N-methylbutanamide

4-[(4-fluorophenyl)methylamino]-N-methyl-N-(2-{4-[5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl}benzyl)butanamide

4-(5-fluoro-2,3-dihydro-1H-indolyl-1-yl)-N-(2-isopropoxybenzyl)-N-methylbutanamide

4-(3,4-dihydroquinolin-1(2H)-yl)-N-(2-isopropoxybenzyl)-N-methylbutanamide

4-(5-fluoro-2,3-dihydro-1H-indolyl-1-yl)-N-(2-methoxybenzyl)-N-methylbutanamide

4-[(4-fluorophenyl)(2-morpholin-4-ylethyl)amino]-N-(2-methoxybenzyl)-N-methylbutanamide

4-[cyclopropyl(4-fluorophenyl)amino]-N-(2-methoxybenzyl)-N-methylbutanamide

4-[ethyl(4-fluorophenyl)amino]-N-(2-methoxybenzyl)-N-methylbutanamide

N-(2,5-difluorobenzyl)-4-[(4-fluorophenyl)thio]-N-methylbutanamide

N-3,4-dihydro-2H-chromen-4-yl-4-[(4-fluorophenyl)thio]-N-methylbutanamide

4-[(4-fluorophenyl)thio]-N-methyl-N-1-naphthylbutanamide

4-[(4-fluorophenyl)thio]-N-methyl-N-1,2,3,4-tetrahydronaphthalen-1-ylbutanamide

N-(5-fluoro-2-methoxybenzyl)-4-[(4-fluorophenyl)thio]-N-methylbutanamide

N-(5-fluoro-2-isopropoxybenzyl)-4-[(4-fluorophenyl)thio]-N-methylbutanamide

4-[(4-fluorophenyl)amino]-N-(2-methoxybenzyl)-N-methylbutanamide

4-[(4-fluorophenyl)thio]-N-(1H-indol-7-ylmethyl)-N-methylbutanamide

N-(6-fluoro-3,4-dihydro-2H-chromen-4-yl)-4-[(4-fluorophenyl)thio]-N-methylbutanamide

N-(5-fluoro-2-methoxybenzyl)-4-[(4-methoxyphenyl)thio]-N-methylbutanamide

N-(2,6-dimethoxybenzyl)-4-[(4-fluorophenyl)thio]-N-methylbutanamide

N-(2-fluoro-5-methoxybenzyl)-4-[(4-fluorophenyl)thio]-N-methylbutanamide

N-[2-(allyloxy)benzyl]-4-[(4-fluorophenyl)thio]-N-methylbutanamide

N-(5-allyl-2-hydroxy-3-methoxybenzyl)-4-[(4-fluorophenyl)thio]-N-methylbutanamide

N-[(4-bromothien-2-yl)methyl]-4-[(4-fluorophenyl)thio]-N-methylbutanamide

N-(5-bromo-2-methoxybenzyl)-4-[(4-fluorophenyl)thio]-N-methylbutanamide

4-[(4-bromophenyl)thio]-N-(5-fluoro-2-methoxybenzyl)-N-methylbutanamide

N-(5-Fluoro-2-methoxybenzyl)-4-[4-(4-fluorophenyl)pyrazol-1-yl]-N-methylbutanamide

N-(5-Fluoro-2-methoxybenzyl)-4-[4-(4-fluorophenyl)-3-methylpyrazol-1-yl]-N-methylbutanamide

N-(5-Fluoro-2-methoxybenzyl)-4-[4-(4-fluorophenyl)-3,5-dimethylpyrazol-1-yl]-N-methylbutanamide

N-(5-Chloro-2-methoxybenzyl)-4-[4-(4-fluorophenyl)pyrazol-1-yl]-N-methylbutanamide

N-(5-Fluoro-2-methoxybenzyl)-4-[4-(4-methoxyphenyl)pyrazol-1-yl]-N-methylbutanamide

N-(5-Fluoro-2-methoxybenzyl)-4-[4-(4-fluoro-2-methylphenyl)pyrazol-1-yl]-N-methylbutanamide

N-(5-Fluoro-2-methoxybenzyl)-4-[4-(4-hydroxyphenyl)pyrazol-1-yl]-N-methylbutanamide

N-(5-Fluoro-2-methoxybenzyl)-4-[4-(4-cyanophenyl)pyrazol-1-yl]-N-methylbutanamide

N-(5-Fluoro-2-methoxybenzyl)-4-(4-pyridin-4-yl-pyrazol-1-yl)-N-methylbutanamide

4-[4-(4-Fluorophenyl)pyrazol-1-yl]-N-isoquinolin-1-yl-N-methylbutamide

N-(5-Fluoro-2-methoxybenzyl)-4-[5-(4-methoxyphenyl)oxazol-2-yl]-N-methylbutanamide

N-(5-Fluoro-2-methoxybenzyl)-4-[3-(4-fluorophenyl)pyrazol-1-yl]-N-methylbutamide

N-(5-Fluoro-2-methoxybenzyl)-4-[3-(4-methoxyphenyl)pyrazol-1-yl]-N-methylbutamide

4-[(4-fluorophenyl)thio]-N-[2-(2-furyl)benzyl]-N-methylbutanamide

N-[(6-fluoro-4H-1,3-benzodioxin-8-yl)methyl]-4-[(4-fluorophenyl)thio]-N-methylbutanamide

4-(5-fluoro-1H-indol-1-yl)-N-(5-fluoro-2-methoxybenzyl)-N-methylbutanamide

4-[(4-fluorophenyl)thio]-N-(2-methoxy-5-methylbenzyl)-N-methylbutanamide

4-[(4-fluorophenyl)thio]-N-[5-methoxy-2-(pyrazol-1-yl)benzyl]-N-methylbutanamide

4-[(4-fluorophenyl)thio]-N-[2-(pyrazol-1-yl)-5-methylbenzyl]-N-methylbutanamide

N-(5-chloro-2-methoxy-3-methylbenzyl)-4-[(4-fluorophenyl)thio]-N-methylbutanamide

N-[2-(allyloxy)-5-chlorobenzyl]-4-[(4-fluorophenyl)thio]-N-methylbutanamide

N-[(5-bromo-2,3-dihydro-1-benzofuran-7-yl)methyl]-4-[(4-fluorophenyl)thio]-N-methylbutanamide

4-[(4-fluorophenyl)thio]-N-isoquinolin-1-yl-N-methylbutanamide

N-(5-fluoro-2-methoxybenzyl)-4-[(4-hydroxyphenyl)sulfinyl]-N-methylbutanamide

N-(5-fluoro-2-methoxybenzyl)-N-methyl-4-[(4-methylphenyl)thio]butanamide

4-[(4-chlorophenyl)thio]-N-(5-fluoro-2-methoxybenzyl)-N-methylbutanamide

N-(5-fluoro-2-methoxybenzyl)-4-[(4-methoxyphenyl)sulfinyl]-N-methylbutanamide

N-(5-chloro-2-methoxybenzyl)-4-[(4-isopropoxyphenyl)thio]-N-methylbutanamide

methyl 4-({4-[(5-fluoro-2-methoxybenzyl)methylamino]-4-oxobutyl}thio)benzoate

N-(5-fluoro-2-methoxybenzyl)-4-{[4-(hydroxymethyl)phenyl]thio}-N-methylbutanamide

4-(5-cyano-1H-indol-1-yl)-N-(5-fluoro-2-methoxybenzyl)-N-methylbutanamide

4-[(4-fluorophenyl)thio]-N-methyl-N-quinolin-8-ylbutanamide

4-(5-chloro-1H-indol-1-yl)-N-(5-fluoro-2-methoxybenzyl)-N-methylbutanamide

4-(5-bromo-1H-indol-1-yl)-N-(5-fluoro-2-methoxybenzyl)-N-methylbutanamide

N-(5-fluoro-2-methoxyphenyl)-4-[(4-fluorophenyl)thio]-N-methylbutanamide

4-[(4-fluorophenyl)thio]-N-isoquinolin-5-yl-N-methylbutanamide

N-(5-fluoro-2-methoxybenzyl)-4-(5-methoxy-1H-indol-1-yl)-N-methylbutanamide

4-[(4-methoxyphenyl)thio]-N-[2-(pyrazol-1-yl)-5-methylbenzyl]-N-methylbutanamide

N-(5-fluoro-2-isopropoxybenzyl]-4-[(4-methoxyphenyl)thio]-N-methylbutanamide

4-[(4-methoxyphenyl)thio]-N-[2-methoxy-5-methylbenzyl]-N-methylbutanamide

4-(5-fluoro-1H-indol-1-yl)-N-(2-methoxy-5-methylbenzyl)-N-methylbutanamide

4-(4-cyano-1H-indol-1-yl)-N-(5-fluoro-2-methoxybenzyl)-N-methylbutanamide

4-(6-fluoro-1H-indol-1-yl)-N-(2-methoxy-5-methylbenzyl)-N-methylbutanamide

4-[(4-methoxyphenyl)thio]-N-[5-methyl-2-(morpholin-4-yl)benzyl]-N-methylbutanamide

N-(5-chloro-2-methoxybenzyl)-5-(4-methoxyphenyl)-N-methyl-5-oxopentanamide

4-(5-fluoro-1H-indol-1-yl)-N-(2-(furan-2-yl)benzyl)-N-methylbutanamide

N-(5-chloro-2-methoxybenzyl)-4-[(4-methoxyphenyl)thio]-N-methylbutanamide

4-(5-fluoro-1H-indol-1-yl)-N-methyl-N-1-naphthylbutanamide

N-isoquinolin-1-yl-4-[(4-methoxyphenyl)thio]-N-methylbutanamide

N-(5-chloro-2-methoxybenzyl)-4-[(4-methoxyphenyl)sulfinyl]-N-methylbutanamide

4-[(4-fluorophenyl)sulfinyl]-N-isoquinolin-1-yl-N-methylbutanamide

N-isoquinolin-1-yl-4-[(4-methoxyphenyl)sulfinyl]-N-methylbutanamide

Ethyl 5-fluoro-2-({4-[(3-fluorophenyl)(methyl)amino]-4-oxobutyl}thio)benzoate

4-[(4-fluorophenyl)thio]-N-[2-(2-furyl)benzyl]-N-methylbutanamide

N-[(6-fluoro-4H-1,3-benzodioxin-8-yl)methyl]-4-[(4-fluorophenyl)thio]-N-methylbutanamide

4-(5-fluoro-1H-indol-1-yl)-N-(5-fluoro-2-methoxybenzyl)-N-methylbutanamide

4-[(4-fluorophenyl)thio]-N-(2-methoxy-5-methylbenzyl)-N-methylbutanamide

4-[(4-fluorophenyl)thio]-N-[5-methoxy-2-(pyrazol-1-yl)benzyl]-N-methylbutanamide

4-[(4-fluorophenyl)thio]-N-[5-methyl-2-(pyrazol-1-yl)benzyl]-N-methylbutanamide

N-(5-chloro-2-methoxy-3-methylbenzyl)-4-[(4-fluorophenyl)thio]-N-methylbutanamide

N-[2-(allyloxy)-5-chlorobenzyl]-4-[(4-fluorophenyl)thio]-N-methylbutanamide

N-[(5-bromo-2,3-dihydro-1-benzofuran-7-yl)methyl]-4-[(4-fluorophenyl)thio]-N-methylbutanamide

4-[(4-fluorophenyl)thio]-N-isoquinolin-1-yl-N-methylbutanamide

N-(5-fluoro-2-methoxybenzyl)-4-[(4-hydroxyphenyl)sulfinyl]-N-methylbutanamide

N-(5-fluoro-2-methoxybenzyl)-N-methyl-4-[(4-methylphenyl)thio]butanamide

4-[(4-chlorophenyl)thio]-N-(5-fluoro-2-methoxybenzyl)-N-methylbutanamide

N-(5-fluoro-2-methoxybenzyl)-4-[(4-methoxyphenyl)sulfinyl]-N-methylbutanamide

N-(5-chloro-2-methoxybenzyl)-4-[(4-isopropoxyphenyl)thio]-N-methylbutanamide

methyl 4-({4-[(5-fluoro-2-methoxybenzyl)methylamino]-4-oxobutyl}thio)benzoate

N-(5-fluoro-2-methoxybenzyl)-4-{[4-(hydroxymethyl)phenyl]thio}-N-methylbutanamide

4-(5-cyano-1H-indol-1-yl)-N-(5-fluoro-2-methoxybenzyl)-N-methylbutanamide

4-[(4-fluorophenyl)thio]-N-methyl-N-quinolin-8-ylbutanamide

4-(5-chloro-1H-indol-1-yl)-N-(5-fluoro-2-methoxybenzyl)-N-methylbutanamide

4-(5-bromo-1H-indol-1-yl)-N-(5-fluoro-2-methoxybenzyl)-N-methylbutanamide

N-(5-fluoro-2-methoxyphenyl)-4-[(4-fluorophenyl)thio]-N-methylbutanamide

4-[(4-fluorophenyl)thio]-N-isoquinolin-5-yl-N-methylbutanamide

N-(5-fluoro-2-methoxybenzyl)-4-(5-methoxy-1H-indol-1-yl)-N-methylbutanamide

4-[(4-methoxyphenyl)thio]-N-[2-(pyrazol-1-yl)-5-methylbenzyl]-N-methylbutanamide

N-(5-fluoro-2-isopropoxybenzyl]-4-[(4-methoxyphenyl)thio]-N-methylbutanamide

N-(5-fluoro-2-methoxybenzyl)-4-[(4-methoxyphenyl)sulfinyl]-N-methylbutanamide

4-[(4-methoxyphenyl)thio]-N-[2-methoxy-5-methylbenzyl]-N-methylbutanamide

4-(5-fluoro-1H-indol-1-yl)-N-(2-methoxy-5-methylbenzyl)-N-methylbutanamide

4-(4-cyano-1H-indol-1-yl)-N-(5-fluoro-2-methoxybenzyl)-N-methylbutanamide

4-(6-fluoro-1H-indol-1-yl)-N-(2-methoxy-5-methylbenzyl)-N-methylbutanamide

4-[(4-methoxyphenyl)thio]-N-[5-methyl-2-(morpholin-4-yl)benzyl]-N-methylbutanamide

N-(5-chloro-2-methoxybenzyl)-5-(4-methoxyphenyl)-N-methyl-5-oxopentanamide

4-(5-fluoro-1H-indol-1-yl)-N-(2-(furan-2-yl)benzyl)-N-methylbutanamide

N-(5-chloro-2-methoxybenzyl)-4-[(4-methoxyphenyl)thio]-N-methylbutanamide

4-(5-fluoro-1H-indol-1-yl)-N-methyl-N-1-naphthylbutanamide

N-isoquinolin-1-yl-4-[(4-methoxyphenyl)thio]-N-methylbutanamide

N-(5-chloro-2-methoxybenzyl)-4-[(4-methoxyphenyl)sulfinyl]-N-methylbutanamide

4-[(4-fluorophenyl)sulfinyl]-N-isoquinolin-1-yl-N-methylbutanamide

N-isoquinolin-1-yl-4-[(4-methoxyphenyl)sulfinyl]-N-methylbutanamide

6-methoxy-1-{4-[(4-methoxyphenyl)thio]butanoyl}-1H-indole

Ethyl 5-fluoro-2-((4-(6-methoxy-2,3-dihydro-1H-indol-1-yl)-4-oxobutyl)thio)benzoate

Ethyl 2-((4-(6-methoxy-2,3-dihydro-1H-indol-1-yl)-4-oxobutyl)thio)benzoate

1-(6-methoxy-2,3-dihydro-1H-indol-1-yl)-4-(o-tolylthio)butan-1-one

1-(6-methoxy-2,3-dihydro-1H-indol-1-yl)-4-((4-methoxyphenyl)thio)butan-1-one

Methyl 2-((4-(6-methoxy-2,3-dihydro-1H-indol-1-yl)-4-oxobutyl)thio)benzoate

Methyl 2-[4-(6-methoxy-2,3-dihydro-1H-indol-1-yl)-4-oxobutoxy]benzoate

1-(6-methoxy-2,3-dihydro-1H-indol-1-yl)-4-((2-methoxyphenyl)thio)butan-1-one

5-fluoro-2-{[4-(6-methoxy-2,3-dihydro-1H-indol-1-yl)-4-oxobutyl]thio}benzoic acid

Ethyl5-fluoro-2-(4-(6-methoxy-2,3-dihydro-1H-indol-1-yl)-4-oxobutyl)sulfinyl)benzoate

Ethyl5-fluoro-2-(4-(6-methoxy-2,3-dihydro-1H-indol-1-yl)-4-oxobutyl)sulfonyl)benzoate

Ethyl 5-fluoro-2-({4-[(3-fluorophenyl)(methyl)amino)-4-oxobutyl}thio)benzoate

1-(4-{[4-fluoro-2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]thio}butanoyl)-6-methoxyindoline

Ethyl 5-fluoro-2-({4-[(3-methoxyphenyl)(methyl)amino]-4-oxobutyl}thio)benzoate

Ethyl 5-fluoro-2-({4-[(2-methoxyphenyl)(methyl)amino]-4-oxobutyl}thio)benzoate

Ethyl 5-fluoro-2-({4-[(4-methoxyphenyl)(methyl)amino]-4-oxobutyl}thio)benzoate

6-methoxy-1-(4-{[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]thio}butanoyl)indoline

6-methoxy-1-(4-{[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]sulfonyl}butanoyl)indoline

6-methoxy-1-(4-{[2-(methoxymethyl)phenyl]thio}butanoyl)indoline

Ethyl 2-[4-(6-methoxy-2,3-dihydro-1H-indol-1-yl)-4-oxobutoxy]benzoate

as well as its racemates, stereoisomers or pharmaceutically acceptable salts.

18. A process of preparation of a compound of formula (I) according to claim 1, where R1 is O, comprising the step of reacting a corresponding compound of formula (II) with a corresponding compound of formula (III), or a precursor thereof:

19. Process of preparation of a compound according to claim 1, where X represents a —

NT- comprising the step of reacting a corresponding compound of formula (IV) with a corresponding compound of formula (V) or a precursor thereof;

20. Process of preparation of a compound according to claim 1, where X represents a —

U—

group comprising the step of reacting a corresponding compound of formula (VI) with a corresponding compound of formula (VII), or precursors thereof;

21. Process of preparation of a compound according to claim 1, where X represents a —

U—

group, U being an oxazole group, comprising the step of cyclizing a corresponding compound of formula (X);

22. Process of preparation of a compound according to claim 1, where X represents a O, —

S(O)_q—

or —

U—

group can comprise the step of reacting a corresponding compound of formula (XIII) with a corresponding compound of formula (XIV), or precursors thereof;

23. Process according to claim 18 further comprising the step of isolating the obtained compound.

25. The pharmaceutical composition comprising compound according to any one of claims 2 to 17, and a pharmaceutically acceptable carrier.

27. A method for treating and/or preventing a viral infection comprising a step of administering to a patient in need thereof a compound according to an one of claims 2 to 17.

24. A pharmaceutical composition comprising a compound of formula (I):

26. A method for treating and/or preventing viral infections comprising a step of administering to a patient in need thereof a compound of formula (I):

28. A method as defined in claim 26, wherein said viral infection is caused by a retrovirus.

29. A method according to claim 28, wherein said viral infection is HIV infection.

30. A combination of a compound as defined in claim 26 with one or more agent(s) and/or pharmaceutical composition(s) useful for the treatment and/or prevention of viral infections and/or disorders.

31. The combination according to claim 30, wherein said agent(s) and/or pharmaceutical composition(s) are useful for the treatment and/or prevention of HIV infection.