4-Aminopiperidine and their use as a medicine

Compounds of general formula I according to any of the preceding claims, wherein R1 represents a linear or branched (C1-C6)alkyl radical, the —(CH2)m—Y—Z11 or —(CH2)m—Z12 radical in which

• Z11represents a (C1-C6)alkyl,
• Z12 represents naphthyl, morpholino, bis-phenyl, pyrrolidinyl substituted by the oxy radical, or the phenyl, piperazinyl, pyridinyl and indolyl radicals which are optionally substituted by one or more substituents chosen independently from the bromo, fluoro, chloro, alkyl, alkoxy, —CF3, —OCF3 radicals;
• or Z12 represents
• 2469
• Y represents the oxygen atom,
• or R1 represents a radical of formula given below:
• 2470

Compounds of general formula I according to any of the preceding claims, wherein R2 represents a radical of formula —C(Y)NHX1, —C(O)X2 or SO2X3 in which

• X1 represents a linear or branched (C1-C10)alkyl, or —(CH2)pZ22 radical in which
• Z22 represents cyclohexyl, cyclohexenyl, bis-phenyl, morpholino, piperidino, mono- or di-alkylamino, —C(O)—O-alkyl, or phenyl, naphthyl or furyl optionally substituted by one or more radicals chosen independently from the fluoro, chloro, bromo, iodo, alkyl, alkoxy, alkylthio, CF3, —OCF3, nitro, cyano, azido, piperidinosulphonyl, —C(O)—O-alkyl, —C(O)-alkyl or phenyl radicals,
• or Z22 represents a radical of formula
• 2471
• X2 represents an alkyl, alkynyl, —(CH2)m—W—(CH2)q—Z23 or —(CH2)pZ24 radical in which
• W represents SO2;
• Z23 represents the phenyl radical;
• Z24 represents cyclohexenyl, bis-phenyl, cyclohexyl optionally substituted by an aminoalkyl, or phenyl, naphthyl, benzothienyl, thienyl or indolyl radical optionally substituted by one or more radicals chosen from fluoro, chloro, bromo, iodo, alkyl, alkoxy, —CF3, —OCF3, —SCF3, hydroxy, —O—C(O)-alkyl, —NH—C(O)-alkyl, mono- or di-alkylamino, amino, or
• Z24 represents a radical of formula
• 2472
• or X2 represents
• 2473
• X3 represents a —(CH2)pZ25 radical in which Z25 represents the phenyl radical optionally substituted by one or more identical or different radicals chosen from alkoxy and CF3,

Compounds of general formula I according to any of the preceding claims, wherein R3 represents the hydrogen atom, an alkyl, alkenyl or furyl-methyl radical substituted by one or more nitro radicals, or a radical of formula —C(Y)—NHX1, —C(O)X2 or SO2X3 in which

• X1 represents a —(CH2)pZ22 radical in which
• Z22 represents the phenyl or naphthyl radical optionally substituted by one or more radicals chosen independently from the fluoro, chloro, bromo, iodo, alkyl, alkoxy, CF3, nitro, phenoxy radicals,
• X2 represents the vinyl radical substituted by a phenyl radical itself optionally substituted by one or more halo, or —(CH2)p—U—Z24 radicals in which
• Z24 represents alkyl, cyclohexyl, tetrahydrofuryl, bis-phenyl, amino, mono or di-alkylamino, or phenyl, indolyl, thienyl, pyridinyl, benzothienyl and furyl optionally substituted by one or more radicals chosen from alkoxy, bromo, chloro, fluoro, amino, mono- and di-alkylamino, nitro, hydroxy, pyrrolyl
• or X2 represents a radical of formula
• 2474
• X3 represents a linear or branched (C1-C10)alkyl radical, the vinyl radical substituted by a phenyl, CF3, or —(CH2)pZ25 radical in which
• Z25 represents a phenyl, naphthyl, thienyl, pyrazolyl or thiazolyl radical optionally substituted by one or more substituents chosen independently from the fluoro, chloro, bromo, iodo, alkyl, alkoxy, CF3, nitro, —NH—C(O)-alkyl, mono- and di-alkylamino radicals;

Compounds of general formula I according to any of the preceding claims, wherein R2 represents the radicals of formula —C(Y)NHX1 and —C(O)X2 in which

• Y represents S;
• X1 represents a phenyl radical optionally substituted by one or more azido radicals,
• X2 represents —(CH2)pZ24 in which
• p is equal to 1, 2 or 3,
• Z24 represents cyclohexyl, or phenyl or benzothienyl optionally substituted by one or more radicals chosen from fluoro, chloro, bromo, iodo or —CF3.

Use of compounds of general formula Ia

• 2489
• in racemic, enantiomeric form or all combinations of these forms, in which:
• R1a represents a linear or branched (C1-C16)alkyl, alkenyl, alkynyl, —(CH2)m—Y—Z11 or —(CH2)m—Z12 radical in which
• Z11 represents a (C1-C6)alkyl or aryl optionally substituted,
• Z12 represents cyano, cyclohexenyl, bis-phenyl, (C3-C7)cycloalkyl, optionally substituted (C3-C7) heterocycloalkyl, optionally substituted aryl or optionally substituted heteroaryl,
• or Z12 represents a radical of formula
• 2490
• or R1a represents a radical of formula
• 2491
• R2a represents a radical of formula —C(Y)NHX1, —C(O)X2 or SO2X3;
• R3a represents the hydrogen atom, an optionally substituted alkyl, alkenyl, alkynyl, optionally substituted aralkyl, optionally substituted heteroarylalkyl radical, or a radical of formula —C(Y)—NHX1, —(CH2)n—C(O)X2, SO2X3 or
• 2492
• X1 represents a linear or branched (C1-C15)alkyl, alkenyl, alkynyl, —(CH2)m—Y—Z21 or —(CH2)pZ22 radical in which
• Z21 represents a (C1-C6)alkyl
• Z22 represents cyclohexenyl, indanyl, bis-phenyl, (C3-C7)cycloalkyl, (C3-C7)heterocycloalkyl, mono- or di-alkylamino, —C(O)—O-alkyl, or aryl or heteroaryl optionally substituted,
• or Z22 represents a radical of formula
• 2493
• X2 represents a linear or branched (C1-C10)alkyl radical, an alkenyl radical optionally substituted by a phenyl radical (the phenyl radical being itself optionally substituted), an alkynyl radical, or a radical of formula —(CH2)m—W—(CH2)q—Z23 or —(CH2)p—U—Z24 in which
• Z23 represents a (C1-C6)alkyl or aryl optionally substituted;
• Z24 represents alkyl, cyclohexenyl, bis-phenyl, (C3-C7)cycloalkyl optionally substituted, (C3-C7)heterocycloalkyl, cyano, amino, mono or di-alkylamino, or aryl or heteroaryl optionally substituted,
• or Z24 represents a radical of formula
• 2494
• or X2 represents a radical represented below:
• 2495
• where the protective group (PG) represents H or tert-butyloxycarbonyl;
• X3 represents a linear or branched (C1-C10)alkyl radical, an alkenyl radical optionally substituted by a phenyl radical (the phenyl radical being itself optionally substituted), CF3, or —(CH2)pZ25 in which
• Z25 represents aryl or heteroaryl optionally substituted,
• or X3 represents a radical of formula
• 2496
• optionally substituted by one or more halo radicals identical or different;
• Y represents an oxygen or sulphur atom;
• W represents an oxygen or sulphur atom, or SO2;
• U represents a covalent bond or the oxygen atom;
• n is an integer from 0 to 4;
• m is an integer from 1 to 6;
• p is an integer from 0 to 6;
• q is an integer from 0 to 2,
• or their addition salts with pharmaceutically acceptable mineral or organic acids, for the preparation of a medicament intended to treat pathological states or diseases in which one (or more) receptor(s) of somatostatin is (are) involved.