# US 2018/0021318 A9 · Piperidine derivatives as human papilloma virus inhibitors

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- Number: US 2018/0021318 A9
- Document ID: US20180021318A9
- Status: Published application
- Kind: A9
- Application number: 15/276,208
- Filed: 2016-09-26
- Published: 2018-01-25
- Earliest claimed: 2006-05-19
- Assignees: Aviragen Therapeutics, Inc.
- Applicants: Aviragen Therapeutics, Inc.
- Inventors: Marta BLUMENFELD; Delphine COMPERE; Jean-Michel GAUTHIER
- Web page: https://patentgrep.com/patent/US20180021318A9

## CPC

- A61K 31/445: Non condensed piperidines, e.g. piperocaine
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 15/00: Drugs for genital or sexual disorders (for disorders of sex hormones A61P5/24); Contraceptives
- A61P 17/00: Drugs for dermatological disorders
- A61P 17/12: Keratolytics, e.g. wart or anti-corn preparations
- A61P 31/12: Antivirals
- A61P 31/20: for DNA viruses
- A61P 35/00: Antineoplastic agents
- 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
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present disclosure is directed to antiviral compounds directed against the papilloma virus, to pharmaceutical compositions containing them, to their preparation method and synthesis intermediates, as well as to their use for treating or preventing an infection by the papilloma virus. The present method thus provides an efficient way of treating patients that have lesions associated with an infection by the papilloma virus.

## Claims

### Claim 1

A method for treating an infection by the HPV 6 or HPV 11 papilloma virus comprising the administration to a patient in need thereof of an efficient quantity of a compound of formula (I):
as well as their stereoisomers,
wherein:
G1 is a bond or a saturated or unsaturated, branched or linear hydrocarbon chain comprising 1-4 carbon atoms, optionally substituted with one or two alkyl groups,
G2 is a
group, the N(R) moiety being bound to the nitrogen carrying the groups B and AG1, wherein:
R is hydrogen atom, an alkyl, a haloalkyl group or a radical selected from the group consisting of carbamate, acetyl, dialkylaminomethyl and —CH2—O—CO— Alk,
G is a bond or a saturated or unsaturated, linear or branched hydrocarbon chain comprising 1-4 carbon atoms, optionally substituted with one or two alkyl groups,
W is an oxygen, sulfur or NH,
R1 and R2 are either identical or different, each represent a group selected from the group consisting of a hydrogen atom, a halogen atom, a hydroxyl, thio, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, monoalkylamino, dialkylamino, cycloalkyl, alkyl, and haloalkyl group,
R3 is an acid group or a bioisostere of the acid function selected from the group consisting of a tetrazole, phosphonate, phosphonamide, sulfonate and sulfonamide,
A is an aryl, cycloalkyl, cycloalkenyl group or a heterocycle, each optionally substituted, and
B is an aryl group or a 6-membered heterocycle, each optionally substituted,
as well as their pharmaceutically acceptable salts.

### Claim 2 (depends on 1)

The method according to claim 1, wherein A is substituted with one or two groups, either identical or different, selected from the group consisting of:
a halogen atom,
an alkoxy, alkylthio, haloalkoxy, haloalkylthio, hydroxyl, thio, cyano, amino, monoalkylamino, or dialkylamino group,
an —SOnR′, —COR′, —CO2R′, —OCOR′, —CONR′R″, —NR′COR″ or —NR′SO2R″ group, wherein R′ and R″ each represent independently of each other a hydrogen atom, an alkyl, haloalkyl group, and n has the value 1 or 2,
an alkyl or haloalkyl group, the alkyl group being optionally substituted with a cyano, amino, monoalkylamino, dialkylamino or acylamino group,
an aryl, arylalkyl, —X-aryl, —X-arylalkyl or -Alk-X-aryl group wherein X is —O—, —NH—, —N(Alk)-, —N(COCH3)—, —S—, —SO—, —SO2—, —CO— or —CONH—, each substituted on the aryl portion with one or two substituents, either identical or different, selected from the group consisting of:
a halogen atom,
an alkyl, haloalkyl, alkoxy, haloalkoxy, thio, alkylthio, haloalkylthio, hydroxyl, cyano, acyl, amino, monoalkylamino or dialkylamino, acid, ester, amide, mono- or di-alkylamide group, and
an —SOnR′, —COR′, —CO2R′, —OCOR′, —CONR′R″, —NR′COR″ or —NR′SO2R″ group, wherein R′ and R″ each represent independently of each other a hydrogen atom, an alkyl, haloalkyl group and n has the value 1 or 2,
a heterocycle, -Alk-heterocycle, —X-heterocycle, —X-Alk-heterocycle, or -Alk-X-heterocycle group, wherein X is —O—, —NH—, —N(Alk)-, —N(COCH3)—, —S—, —SO—, —SO2—, —CO—, or —CONH—, each optionally substituted on the heterocycle portion with one or two substituents either identical or different, selected from the group consisting of:
a halogen atom,
an alkyl, haloalkyl, alkoxy, haloalkoxy, thio, alkylthio, haloalkylthio, hydroxyl, cyano, acyl, amino, mono alkylamino or dialkylamino, acid, ester, amide, mono- or di-alkylamide group, and
an —SOnR′, —COR′, —CO2R′, —OCOR′, —CONR′R″, —NR′COR″ or NR′SO2R″ group, wherein R′ and R″ each represent independently of each other a hydrogen atom, an alkyl, haloalkyl group and n has the value 1 or 2; and
a cycloalkyl, -Alk-cycloalkyl, cycloalkenyl, -Alk-cycloalkenyl, —X-cycloalkyl, —X-Alk-cycloalkyl, —X-cycloalkenyl, —X-Alk-cycloalkenyl, -Alk-X-cycloalkyl, -Alk-X-cycloalkenyl group, wherein X is —O—, —NH—, —N(Alk)-, —N(COCH3)—, —S—, —SO—, —SO2—, —CO— or —CONH— each optionally substituted on the cyclic portion with one or two substituents, either identical or different, selected from the group consisting of:
a halogen atom,
an alkyl, haloalkyl, alkoxy, haloalkoxy, thio, alkylthio, haloalkylthio, hydroxyl, cyano, acyl, amino, monoalkylamino or dialkylamino, acid, ester, amide, mono- or di-alkylamide, or oxo, and
an —SOnR′, —COR′, —CO2R′, —OCOR′, —CONR′R″, —NR′COR″ or NR′SO2R″ group, wherein R′ and R″ each represent independently of each other a hydrogen atom, an alkyl, haloalkyl group and n has the value 1 or 2.

### Claim 3 (depends on 1)

The method according to claim 1, wherein B is a phenyl or 6-membered heterocycle, substituted in the ortho position with a R4 group and optionally substituted with a R5 group, wherein:
R4 is:
an alkyl, —NHAlk, —NAlkAlk′, —NHcycloalkyl or —NAlkcycloalkyl group, Alk and Alk′ being identical or different,
a cycloalkyl, cycloalkenyl, N-cycloalkyl or N-cycloalkenyl group, each optionally substituted with one or two substituents, either identical or different, selected from the group consisting of a halogen atom, an alkyl, haloalkyl, alkoxy, haloalkoxy, thio, alkylthio, haloalkylthio, hydroxyl, cyano, acyl, amino, monoalkylamino or dialkylamino, acid, ester, amide, mono- or dialkylamide, oxo and —X-aryl group and wherein X is —O— an —NH—, —N(Alk)-, —N(COCH3)—, —S—, —SO—, —SO2—, —CO— or —CONH—, or
an aryl group optionally substituted with one or two substituents, either identical or different, selected from the group consisting of a halogen atom, an alkyl, haloalkyl, alkoxy, haloalkoxy, thio, alkylthio, haloalkylthio, hydroxyl, cyano, acyl, amino, monoalkylamino or dialkylamino, acid, ester, amide, mono or dialkylamide and an —X-aryl group, wherein X is —O—, —NH—, —N(Alk)-, —N(COCH3)—, —S—, —SO—, —SO2—, —CO— or —CONH—, and
R5 is:
a halogen atom,
a hydroxyl, alkoxy, haloalkoxy, thio, alkylthio, haloalkylthio, amino, monoalkylamino, dialkylamino, —NHacyl, cyano, acyl, acid, ester, amide, monoalkylamide or dialkylamide group,
an alkyl or haloalkyl group, the alkyl group may be substituted with a cyano, hydroxyl, alkoxy, acid or ester group,
a —SOnAlk, —SOnH2, —SOnNHAlk or —SOnNAlkAlk′ group, wherein n has the value of 1 or 2 and Alk and Alk′ are either identical or different, or
a piperidine, oxopiperidine, morpholine group, or else a piperazine group optionally substituted with an alkyl or acyl group.

### Claim 4 (depends on 1)

The method according to claim 1, wherein:
A is a phenyl or heterocycle group, each optionally substituted with one or two groups, either identical or different, selected from the group consisting of:
a halogen atom,
an alkoxy, alkylthio, haloalkoxy, haloalkylthio, hydroxyl, thio, cyano, amino, monoalkylamino or dialkylamino group,
a —SOnR′, —COR′—, —CO2R′, —OCOR′, —CONR′R″, —NR′COR″ or —NR′SO2R″ group, wherein R′ and R″ each represent independently of each other a hydrogen atom, an alkyl, haloalkyl group, and n has the value 1 or 2,
an alkyl or haloalkyl group, the alkyl group being optionally substituted with a cyano, amino, monoalkylamino, dialkylamino or acylamino group,
an aryl, arylalkyl, —X-aryl group, wherein X is —O—, —NH—, —N(Alk)-, —N(COCH3)—, —S—, —SO—, —SO2—, —CO— or —CONH— group, each substituted on the aryl portion with one or two substituents, either identical or different, selected from the group consisting of:
a halogen atom,
an alkyl, haloalkyl, alkoxy, haloalkoxy, thio, alkylthio, haloalkylthio, hydroxyl, cyano, acyl, amino, monoalkylamino or di-alkyl amino, acid, ester, amide, mono- or dialkylamide group, and
an —SOnR′, —COR′, —CO2R′, —OCOR′, —CONR′R″, —NR′COR″ or —NR′SO2R″ group, wherein R′ and R″ each represent independently of each other a hydrogen atom, an alkyl, haloalkyl group, and n has the value 1 or 2,
a heterocycle, —X-heterocycle group wherein X is —O—, —NH—, —N(Alk)-, —N(COCH3)—, —S—, —SO—, —SO2—, —CO— or —CONH—, each optionally substituted on the heterocycle portion with one or two substituents, either identical or different, selected from the group consisting of:
a halogen atom,
an alkyl, haloalkyl, alkoxy, haloalkoxy, thio, alkylthio, haloalkylthio, hydroxyl, cyano, acyl, amino, monoalkylamino or dialkylamino, acid, ester, amide, mono- or di-alkylamide group, and
an —SOnR′, —COR′, —CO2R′, —OCOR′, —CONR′R″, —NR′COR″ or —NR′SO2R″ group, wherein R′ and R″ each represent independently of each other a hydrogen atom, an alkyl, haloalkyl group, and n has the value 1 or 2;
and
a cycloalkyl, cycloalkenyl, —X-cycloalkyl, —X-cycloalkenyl group wherein X is —O—, —NH—, —N(Alk)-, —N(COCH3)—, —S—, —SO—, —SO2—, —CO— or —CONH— group, each optionally substituted on the cyclic portion with one or two substituents, either identical or different, selected from the group consisting of:
a halogen atom,
an alkyl, haloalkyl, alkoxy, haloalkoxy, thio, alkylthio, haloalkylthio, hydroxyl, cyano, acyl, amino, monoalkylamino or dialkylamino, acid, ester, amide, mono- or di-alkylamide, or oxo group, and
an —SOnR′, —COR′, —CO2R′, —OCOR′, —CONR′R″, —NR′COR″ or —NR′SO2R″ group, wherein R′ and R″ each represent independently of each other a hydrogen atom, an alkyl, haloalkyl group, and n has the value 1 or 2; and
B is a phenyl or pyridine group:
substituted in the ortho position with an N-cycloalkyl group, a heterocycle or with a cyclohexyl, each optionally substituted with one or two substituents, either identical or different, selected from the group consisting of an alkyl, haloalkyl, alkoxy, haloalkoxy, —X-aryl group, where X is —O—, —NH—, —N(Alk)-, —N(COCH3)—, —S—, —SO—, —SO2—, —CO— and —CONR—, and/or
optionally substituted with a halogen atom or with an alkyl or haloalkyl group.

### Claim 5 (depends on 4)

The method according to claim 4, wherein B is:
substituted in the ortho position with a piperidine group or with a cyclohexyl, each optionally substituted with one or two substituents, either identical or different, selected from the group consisting of an alkyl, haloalkyl, alkoxy, haloalkoxy, —X-aryl group, where X is —O—, —NH—, —N(Alk)-, —N(COCH3)—, —S—, —SO—, —SO2—, —CO— and —CONH—, and/or
optionally substituted with a halogen atom or with an alkyl or haloalkyl group.

### Claim 6 (depends on 1)

The method according to claim 1, wherein:
G2 is a
group,
wherein n is an integer comprised between 1 and 4 and m is an integer having the value 1 or 2,
R1 is an alkoxy group,
R2 is a hydrogen or halogen atom, or an alkyl group,
R3 is an acid or ester group,
A is an aryl group optionally substituted:
in the meta or para position with:
a halogen atom or an alkyl, haloalkyl, cyano, alkoxy, haloalkoxy, acylaminoalkyl group or an —XR group, wherein X is —O—, —NH—, —N(Alk)-, —N(COCH3)—, —S—, —SO—, —SO2—, —CO— or —CONH— group, and R is an arylalkyl, cycloalkyl or aryl group, each optionally substituted with one or two substituents, either identical or different, chosen among a halogen atom, an alkoxy, alkyl, haloalkyl, cyano, acyl, amino, monoalkylamino or dialkylamino, acid, ester, amide, mono- or di-alkylamide group, or a —SOnR′, —OCOR′, —NR′COR″ or —NR′SO2″ group, wherein R′ and R″ each represent independently of each other a hydrogen atom, an alkyl, haloalkyl group, and n has the value 1 or 2,
a cycloalkyl, aryl, arylalkyl group or heterocycle, each being optionally substituted with one or two substituents, either identical or different, chosen among a halogen atom, an alkoxy, alkyl, haloalkyl, cyano, acyl, amino, monoalkylamino or dialkylamino, acid, ester, amide, mono- or di-alkylamide group, or a —SOnR′, —OCOR′, —NR′COR″, or —NR′SO2R″ group, wherein R′ and R″ each represent independently of each other a hydrogen atom, an alkyl, haloalkyl group and n has the value 1 or 2,
and/or in the ortho or meta position with an alkyl group, and
B is an aryl group,
substituted in the ortho position with a heterocycle, and/or
substituted in the ortho′ position with an alkyl group.

### Claim 7 (depends on 1)

The method according to claim 1, wherein:
G1 is a bond or a saturated or unsaturated, linear or branched hydrocarbon chain comprising 1-4 carbon atoms, optionally substituted with one or two alkyl groups,
G2 is a
group,
wherein n is an integer comprised between 1 and 4 and m is an integer having the value 1 or 2,
R1 is an alkoxy group,
R2 is a hydrogen or halogen atom, or an alkyl group,
R3 is an acid or ester group,
A is an aryl group optionally substituted:
in the meta or para position with:
a halogen atom or a cyano, alkoxy, haloalkoxy, acylaminoalkyl or —XR group, wherein:
X is —O—, —S—, —SO—, —SO2—, or —CO— and
R is an arylalkyl, cycloalkyl or aryl group, each optionally substituted with one or two substituents, either identical or different, chosen among a halogen atom, an alkoxy or acyl group, or
a cycloalkyl, aryl or arylalkyl group, each optionally substituted with one or two substituents, either identical or different, chosen among an acyl or alkoxy group, and
and/or in the ortho or meta position with an alkyl group, and
B is an aryl group,
substituted in the ortho position with a heterocycle, and/or
substituted in the ortho′ position with an alkyl group.

### Claim 8 (depends on 7)

The method according to claim 7, wherein:
B is a phenyl, and
A is a phenyl optionally substituted in the para position with an arylalkyl.

### Claim 9 (depends on 8)

The method according to claim 8, wherein:
A is a benzylphenyl.

### Claim 10 (depends on 7)

The method according to claim 7, wherein G1 is a bond or a hydrocarbon chain comprising 1 or 2 carbon atoms.

### Claim 11 (depends on 7)

The method according to claim 7, wherein n has the value 1 or 2.

### Claim 12 (depends on 7)

The method according to claim 7, wherein R1 is in the ortho position relatively to R3.

### Claim 13 (depends on 7)

The method according to claim 7, wherein R2 is in the meta position relatively to R3.

### Claim 14 (depends on 7)

The method according to claim 7, wherein B is a phenyl group,
substituted in the ortho position with a piperidine group, and/or
substituted in the ortho′ position with an alkyl group.

### Claim 15 (depends on 1)

The method according to claim 1, wherein the compound of formula (I) is selected from the group consisting of:
1) 5-bromo-2-methoxy-4-[N′-(4-methoxy-phenyl)-N′-(2-piperidin-1-yl-phenyl)-hydrazinocarbonylmethyl]-benzoic acid hydrochloride
2) 5-bromo-2-methoxy-4-[N′-(2-piperidin-1-yl-phenyl)-N′-(4-trifluoromethoxy-phenyl)-hydrazinocarbonylmethyl]-benzoic acid hydrochloride
3) 5-bromo-2-methoxy-4-[N′-(3-methoxy-benzyl)-N′-(2-piperidin-1-yl-phenyl)-hydrazinocarbonylmethyl]-benzoic acid hydrochloride
4) 4-[N′-(4-benzyloxy-phenyl)-N′-(2-piperidin-1-yl-phenyl)-hydrazinocarbonylmethyl]-5-bromo-2-methoxy-benzoic acid hydrochloride
5) 5-bromo-4-{N′-[4-(4-fluoro-phenoxy)-phenyl]-N′-(2-piperidin-1-yl-phenyl )-hydrazinocarbonylmethyl}-2-methoxy-benzoic acid hydrochloride
6) 5-bromo-2-methoxy-4-{N′-[2-(4-methoxy-phenyl)-ethyl]-N′-2-piperidin-1-yl-phenyl)-hydrazinocarbonylmethyl}-benzoic acid hydrochloride
7) 5-bromo-2-methoxy-4-[N′-(4-methoxy-phenyl)-N′-(2-methyl-6-piperidin-1-yl-phenyl)-hydrazinocarbonyl-methyl]-benzoic acid hydrochloride
7a) Methyl 5-bromo-2-methoxy-4-[N′-(4-methoxy-phenyl)-N′-(2-methyl-6-piperidin-1-yl-phenyl)-hydrazinocarbonyl-methyl]-benzoate
8) 5-bromo-2-methoxy-4-[N′-(4-methoxy-benzyl)-N′-(2-piperidin-1-yl-phenyl)-hydrazinocarbonylmethyl]-benzoic acid hydrochloride
9) 5-bromo-4-[N′-(4-cyclohexyl-phenyl)-N′-(2-piperidin-1-yl-phenyl)-hydrazinocarbonylmethyl]-2-methoxy-benzoic acid hydrochloride
10) 5-bromo-2-methoxy-4-[N′-(2-methyl-6-piperidin-1-yl-phenyl)-N′-(4-trifluoromethoxy-phenyl)-hydrazino-carbonylmethyl]-benzoic acid hydrochloride
11) 5-bromo-2-methoxy-4-[N′-(4′-methoxy-biphenyl-4-yl)-N′-(2-piperidin-1-yl-phenyl)-hydrazinocarbonylmethyl]-benzoic acid hydrochloride
12) 5-bromo-4-[N′-(4-cyclohexyloxy-phenyl)-N′-(2-piperidin-1-yl-phenyl)-hydrazinocarbonylmethyl]-2-methoxy-benzoic acid hydrochloride
13) 5-bromo-2-methoxy-4-[N′-(4-phenoxy-phenyl)-N′-(2-piperidin-1-yl-phenyl)-hydrazinocarbonylmethyl]-benzoic acid hydrochloride
14) 5-bromo-4-{N′-[4-(4-chloro-phenoxy)-phenyl]-N′-(2-piperidin-1-yl-phenyl )-hydrazinocarbonylmethyl}-2-methoxy-benzoic acid hydrochloride
15) 4-{N′-[4-(4-fluoro-phenoxy)-phenyl]-N′-(2-methyl-6-piperidin-1-yl-phenyl)-hydrazinocarbonylmethyl}-2-methoxy-benzoic acid hydrochloride
16) 5-bromo-4-{N′-[4-(4-fluoro-phenoxy)-phenyl]-N′-(2-methyl-6-piperidin-1-yl-phenyl)-hydrazino-carbonyl-methyl}-2-methoxy-benzoic acid hydrochloride
16a) Methyl 5-bromo-4-{N′-[4-(4-fluoro-phenoxy)-phenyl]-N′-(2-methyl-6-piperidin-1-yl-phenyl)-hydrazino-carbonyl-methyl}-2-methoxy-benzoate
17) 4-[N′-(4-benzyl-phenyl)-N′-(2-piperidin-1-yl-phenyl)-hydrazinocarbonylmethyl]-5-bromo-2-methoxy-benzoic acid hydrochloride
18) 4-[N′-(4-bromo-phenyl)-N′-(2-piperidin-1-yl-phenyl)-hydrazinocarbonylmethyl]-5-chloro-2-methoxy-benzoic acid hydrochloride
19) 4-[N′-(3′-acetyl-biphenyl-4-yl)-N′-(2-piperidin-1-yl-phenyl)-hydrazinocarbonylmethyl]-5-chloro-2-methoxy-benzoic acid hydrochloride
20) 4-[N′-(4′-acetyl-biphenyl-4-yl)-N′-(2-piperidin-1-yl-phenyl)-hydrazinocarbonylmethyl]-5-chloro-2-methoxy-benzoic acid hydrochloride
21) 5-bromo-2-methoxy-4-[N′-(3-phenoxy)-phenyl]-N′-(2 piperidin-1-yl-phenyl)-hydrazinocarbonylmethyl]-benzoic acid hydrochloride
22) 5-bromo-2-methoxy-4-[N′-(4-phenylsulfanyl)-phenyl]-N′-(2-piperidin-1-yl-phenyl)-hydrazinocarbonylmethyl]-benzoic acid hydrochloride
23) 4-[N′-(4-benzenesulfonyl-phenyl)-N′-(2-piperidin-1-yl-phenyl)-hydrazinocarbonylmethyl]-5-bromo-2-methoxy-benzoic acid hydrochloride
24) 4-[N′-(4-benzenesulfinyl-phenyl)-N′-(2-piperidin-1-yl-phenyl)-hydrazinocarbonylmethyl]-5-bromo-2-methoxy-benzoic acid hydrochloride
25) 2-methoxy-4-{(E)-2-[N′-(4-methoxy-phenyl)-N′-(2-methyl-6-piperidin-1-yl-phenyl)-hydrazinocarbonyl]-vinyl}-benzoic acid hydrochloride
26) 5-bromo-2-methoxy-4-{(E)-2-[N′-(4-methoxy-phenyl)-N′-(2-methyl-6-piperidin-1-yl-phenyl)-hydrazinocarbonyl]-vinyl}-benzoic acid hydrochloride
27) 4-[N′-(4-benzyl-phenyl)-N′-(2-methyl-6-piperidin-1-yl-phenyl)-hydrazinocarbonylmethyl]-5-bromo-2-methoxy-benzoic acid hydrochloride
28) 5-bromo-2-methoxy-4-[N′-(4′-methoxy-biphenyl-4-yl)-N′-(2-methyl-6-piperidin-1-yl-phenyl)-hydrazino-carbonyl-methyl]-benzoic acid hydrochloride
29) 4-[N′-(acetylamino-methyl)-phenyl]-N′-(2-methyl-6-piperidin-1-yl-phenyl)-hydrazinocarbonylmethyl]-5-bromo-2-methoxy-benzoic acid hydrochloride
30) 4-[N′-(4-benzoyl)-phenyl]-N′-(2-piperidin-1-yl-phenyl)-hydrazinocarbonylmethyl]-5-bromo-2-methoxy-benzoic acid hydrochloride
31) 5-bromo-4-[N′-(4-cyano-phenyl)-N′-(2-methyl-6-piperidin-1-yl-phenyl)-hydrazinocarbonylmethyl]-2-methoxy-benzoic acid hydrochloride
32) 4-[N′-(4′-acetyl-biphenyl-4-yl)-N′-(2-methyl-6-piperidin-1-yl-phenyl)-hydrazinocarbonylmethyl]-5-bromo-2-methoxy-benzoic acid hydrochloride; and
33) 5-bromo-2-methoxy-4-[N′-(4′-methoxy-2-methyl-biphenyl-4-yl)-N′-(2-methyl-6-piperidin-1-yl-phenyl)-hydrazinocarbonylmethyl]-benzoic acid hydrochloride.

### Claim 16 (depends on 1)

The method according to claim 1, wherein the patient has a lesion associated with an infection by the papilloma virus.

### Claim 17 (depends on 1)

The method according to claim 1, wherein the patient has an ano-genital wart, a laryngeal, conjunctive or buccal papilloma, or an epithelial lesion.

### Claim 18 (depends on 17)

The method according to claim 17, wherein said ano-genital wart is an acuminated condyloma or a plane condyloma.

### Claim 19 (depends on 17)

The method according to claim 17, wherein said epithelial lesion is selected from the group consisting of a recurrent respiratory papillomatosis, a low grade or high grade intra-epithelial neoplasia, a bowenoid papulosis, a wart, an epidermodysplasia verruciformis, a carcinoma, and a lesion associated with the papilloma virus.

### Claim 20 (depends on 19)

The method according to claim 19, wherein said wart is selected from the group consisting of a verruca vulgaris, a verruca plantaris, a myrmecia wart, a surface wart and a verruca plana.

### Claim 21 (depends on 19)

The method according to claim 19, wherein said carcinoma is an ano-genital carcinoma.

### Claim 22

A method for treating an infection by the HPV 6 or HPV 11 papilloma virus comprising the administration to a patient in need thereof of an efficient quantity of a compound of formula (I):
as well as their stereoisomers,
wherein:
G1-A represents a phenyl group or a 6-membered heterocycle, each optionally substituted,
G2 is a
group, wherein:
R is a hydrogen atom,
G is a bond or a saturated or unsaturated, linear or branched hydrocarbon chain comprising 1-4 carbon atoms, optionally substituted with one or two alkyl groups,
W is an oxygen, sulfur or NH,
R1 and R2 are either identical or different, each represent a halogen atom or an alkoxyl,
R3 is an acid group, and
B is a phenyl, optionally substituted with one or two alkyl groups and/or a heterocycle,
as well as their pharmaceutically acceptable salts.

### Claim 23 (depends on 22)

The method according to claim 22, wherein the patient has a lesion associated with an infection by the papilloma virus.

### Claim 24 (depends on 22)

The method according to claim 22, wherein the patient has an ano-genital wart, a laryngeal, conjunctive or buccal papilloma, or an epithelial lesion.

### Claim 25 (depends on 24)

The method according to claim 24, wherein said ano-genital wart is an acuminated condyloma or a plane condyloma.

### Claim 26 (depends on 24)

The method according to claim 24, wherein said epithelial lesion is selected from the group consisting of a recurrent respiratory papillomatosis, a low grade or high grade intra-epithelial neoplasia, a bowenoid papulosis, a wart, an epidermodysplasia verruciformis, a carcinoma, and a lesion associated with the papilloma virus.

### Claim 27 (depends on 26)

The method according to claim 26, wherein said wart is selected from the group consisting of a verruca vulgaris, a verruca plantaris, a myrmecia wart, a surface wart and a verruca plana.

### Claim 28 (depends on 26)

The method according to claim 26, wherein said carcinoma is an ano-genital carcinoma.