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US 2005/0239796 A1Published application
Derivatives of 4-aminopiperidine and their use a medicament
AssigneeSociete De Conseils De Recherches Et D'Applications Scientifieques (S.C.R.A.S.)
InventorsChristophe Thurieau, Jerome Gonzalez, Christophe Moinet
Life of this patent
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Abstract
A subject of the present application is new derivatives of 4-aminopiperidines of formula in which R1, R2 and R3 represent various radical, and their preparation processes by synthetic methods in parallel in liquid and solid phase. These products having a good affinity with certain sub-types of somatostatin receptors, they are particularly useful for treating the pathological states or diseases in which one (or more) somatostatin receptors are involved.
Claims26
A compound of the formula
- in racemic, enantiomeric form or all combinations of these forms, wherein
- R1 is selected from the group consisting of (C1-C16)alkyl, alkenyl, alkynyl, —(CH2)m—Y-Z11 and —(CH2)m-Z12,
- Z11 is (C1-C6)alkyl or optionally substituted aryl,
- Z12 is selected from the group consisting of cyano, cyclohexenyl, bis-phenyl, (C3-C7)cycloalkyl, optionally substituted (C3-C7)heterocycloalkyl, optionally substituted aryl or optionally substituted heteroaryl,
- or Z12 is selected from the group consisting of
- or R1 is selected from the group consisting of
- R2 is selected from the group consisting of —C(Y)NHX1, —C(O)X2 and SO2X3;
- R3 is selected from the group consisting of hydrogen, an optionally substituted alkyl, alkenyl, alkynyl, optionally substituted aralkyl, optionally substituted heteroarylalkyl, —C(Y)—NHX1, —(CH2)n—C(O)X2, SO2X3,
- X1 is selected from the group consisting of (C1-C15)alkyl, alkenyl, alkynyl, —(CH2)m—Y-Z21, and —(CH2)pZ22,
- Z21 is (C1-C6)alkyl
- Z22 is selected from the group consisting of cyclohexenyl, indanyl, bis-phenyl, (C3-C7)cycloalkyl, and (C3-C7)heterocycloalkyl, mono- or di-alkylamino, —C(O)—O-alkyl, aryl and heteroaryl optionally substituted,
- or Z22 is
- X2 is selected from the group consisting of (C1-C10)alkyl, alkenyl optionally substituted by phenyl optionally substituted, alkynyl, —(CH2)m—W—(CH2)q-Z23 and —(CH2)p—U-Z24 wherein
- Z23 is (C1-C6)alkyl or aryl optionally substituted;
- Z24 is selected from the group consisting of alkyl, cyclohexenyl, bis-phenyl, (C3-C7)cycloalkyl optionally substituted, (C3-C7)heterocycloalkyl, cyano, amino, mono and di-alkylamino, aryl and heteroaryl optionally substituted,
- or Z24 is selected from the group consisting of
- X2 is selected from the group consisting of
- where the protective group (PG) is H or tert-butyloxycarbonyl;
- X3 is selected from the group consisting of (C1-C10)alkyl, alkenyl optionally substituted by phenyl optionally substituted, —CF3, and —(CH2)pZ25,
- Z25 is aryl or heteroaryl optionally substituted,
- or X3 is
- optionally substituted by at least one halo;
- Y is oxygen or sulfur,
- W is oxygen or sulfur or SO2;
- U is a covalent bond or oxygen;
- 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,
- and their addition salts with pharmaceutically acceptable acids, with the exclusion of compounds of formula I wherein R1 is alkyl, alkenyl or benzyl, R2 is optionally substituted benzyloxy and R3 is aralkyl.
27 more elements
(canceled)
A method of treating a disease involving a receptor of somatostatin in warm-blooded animals comprising administering to warm-blooded animals in need thereof an amount of a compound of the formula
- in racemic, enantiomeric form or all combinations of these forms, wherein
- R1a is selected from the group consisting of (C1-C16)alkyl, alkenyl, alkynyl, —(CH2)m—Y-Z11 and —(CH2)m-Z12,
- Z11 is (C1-C6)alkyl or aryl optionally substituted,
- Z12 is selected from the group consisting of cyano, cyclohexenyl, bis-phenyl, (C3-C7)cycloalkyl, optionally substituted (C3-C7)heterocycloalkyl, optionally substituted aryl and optionally substituted heteroaryl,
- or Z12 is selected from the group consisting of
- or R1a is selected from the group consisting of
- R2a is selected from the group consisting of —C(Y)NHX1, —C(O)X2 and —SO2X3;
- R3a is selected from the group consisting of hydrogen, optionally substituted alkyl, alkenyl, alkynyl, optionally substituted aralkyl, optionally substituted heteroarylalkyl, —C(Y) —NHX1, —(CH2)n—C(O)X2, —SO2X3,
- X1 is selected from the group consisting of (C1-C15)alkyl, alkenyl, alkynyl, (CH2)m—Y-Z21 and —(CH2)pZ22,
- Z1 is (C1-C6)alkyl
- Z22 is selected from the group consisting of cyclohexenyl, indanyl, bis- phenyl, (C3-C7)cycloalkyl, (C3-C7)heterocycloalkyl, mono- or di-alkylamino, —C(O)—O-alkyl and aryl or heteroaryl optionally substituted,
- or Z22 is
- X2 is selected from the group consisting of (C1-C10)alkyl, alkenyl optionally substituted by phenyl unsubstituted or substituted, alkynyl, —(CH2)m—W—(CH2)q-Z23 and —(CH2)p—U-Z24,
- Z23 is (C1-C6)alkyl or aryl optionally substituted;
- Z24 is selected from the group consisting of alkyl, cyclohexenyl, bis-phenyl, (C3-C7)cycloalkyl optionally substituted, (C3-C7)heterocycloalkyl, cyano, amino, mono or di-alkylamino and aryl or heteroaryl optionally substituted,
- or Z24 is selected from the group consisting of
- or X2 is selected from the group consisting of
- where the protective group (PG) is H or tert-butyloxycarbonyl;
- X3 is selected from the group consisting of (C1-C10)alkyl, alkenyl optionally substituted by phenyl unsubstituted or substituted, —CF3 and —(CH2)pZ25,
- Z25 is aryl or heteroaryl optionally substituted,
- or X3 is
- unsubstituted by at least one halogen
- Y is oxygen or sulfur;
- W is selected from the group consisting of oxygen, sulfur and —SO2;
- U is a covalent bond or oxygen;
- 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,
- and their acid addition salts.
27 more elements
Dependencies are inferred from the claim text.