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US 7,741,362 B2Granted
Somatostatin receptor 1 and/or 4 selective agonists and antagonists
AssigneeSiegfried Wurster
InventorsJussi Tomperi, Paivi Hautamaki, Harri Salo, Mia Engstrom, Andrei Tauber, Anna-Marja Hoffren, Siegfried Wurster
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Abstract
The invention relates to (hetero)arylsulfonylamino based peptidomimetics of formula (I), wherein R1, R2, R3, A, B, D, Q, k and n are defined as disclosed, or a pharmaceutically acceptable salt or ester thereof. Compounds of formula (I) possess high affinity and selectivity for the somatostatin receptor subtypes SSTR1 and/or SSTR4 and can be used for the treatment or diagnosis of diseases or conditions wherein an interaction with SSTR1 and/or SSTR4 is indicated to be useful.
Claims13
A compound of Formula II
- or a pharmaceutically acceptable salt or ester thereof,
- wherein
- Q is
- 1) H,
- 2) aryl or
- 3) heteroaryl, wherein aryl and heteroaryl are unsubstituted or substituted with 1 to 4 substituents selected from Ra, or
- 4) a group of formula
- wherein R4 is
- 1) H,
- 2) (C1-C6)alkyl,
- 3) (C2-C6)alkenyl,
- 4) (C2-C6)alkynyl,
- 5) Cy,
- 6) Cy-(C1-C6)alkyl,
- 7) Cy-(C2-C6)alkenyl or
- 8) Cy-(C2-C6)alkynyl, wherein alkyl, alkenyl, alkynyl and Cy are unsubstituted or substituted with 1 or 2 substituents selected from Rd,
- R5 is
- 1) H,
- 2) (C1-C6)alkyl,
- 3) (C2-C6)alkenyl,
- 4) (C2-C6)alkynyl,
- 5) aryl,
- 6) aryl-(C1-C6)alkyl,
- 7) heteroaryl or
- 8) heteroaryl-(C1-C6)alkyl, wherein aryl and heteroaryl are unsubstituted or substituted with 1 to 4 substituents selected from Rd, or
- R4 and R5 together with the atom to which they are attached form a 3- to 8-membered ring containing 0 to 2 heteroatoms selected from the group consisting of N, O and S, wherein said ring is unsubstituted or substituted with 1 to 3 substituents selected from Rd, or said ring is fused to aryl or heteroaryl, either of which is unsubstituted or substituted with 1 to 3 substituents selected from Rd;
- A is
- 1) H,
- 2) (C1-C6)alkyl or
- 3) (C3-C5)cycloalkyl;
- B is independently
- 1) H,
- 2) halogen or
- 3) (C1-C6)alkyl, or
- symbols B together form a double or triple bond between the atoms to which they are attached;
- R1 is
- 1) H,
- 2) (C1-C6)alkyl or
- 3) (C3-C7)cycloalkyl;
- R2 is independently
- 1) H,
- 2) (C1-C6)alkyl,
- 3) (C2-C6)alkenyl,
- 4) (C2-C6)alkynyl,
- 5) (C3-C7)cycloalkyl or
- 6) (C3-C7)cycloalkyl(C1-C6)alkyl, or
- symbols R2 together with the nitrogen to which they are attached form a saturated 5- to 7-membered ring containing 1 or 2 heteroatoms selected from the group consisting of N, O and S;
- R3 is
- 1) H,
- 2) (C1-C6)alkyl,
- 3) (C2-C6)alkenyl,
- 4) (C2-C6)alkynyl or
- 5) (C3-C7)cycloalkyl;
- R6 is independently
- 1) H,
- 2) halogen,
- 3) —NO2,
- 4) —NRbRb,
- 5) —CN,
- 6) —ORb,
- 7) —SRb,
- 8) —C(O)Rb,
- 9) (C1-C6)alkyl,
- 10) (C2-C6)alkenyl,
- 11) (C2-C6)alkynyl,
- 12) (C3-C7)cycloalkyl or
- 13) —CF3;
- Ra is independently
- 1) H,
- 2) halogen,
- 3) —ORb,
- 4) (C1-C6)alkyl or
- 5) —CF3;
- Rb is independently
- 1) hydrogen,
- 2) (C1-C6)alkyl,
- 3) (C2-C6)alkenyl,
- 4) (C2-C6)alkynyl,
- 5) Cy or
- 6) Cy-(C1-C4)alkyl;
- Rd is independently
- 1) a group selected from Rc,
- 2) (C1-C6)alkyl,
- 3) (C2-C6)alkenyl,
- 4) (C2-C6)alkynyl,
- 5) aryl,
- 6) aryl-(C1-C6)alkyl,
- 7) heteroaryl-(C1-C6)alkyl,
- 8) (C3-C7)cycloalkyl or
- 9) heterocyclyl, wherein alkyl, alkenyl, alkynyl, aryl and heteroaryl are unsubstituted or substituted with 1 to 4 substituents independently selected from Rc;
- Rc is independently
- 1) a group selected from Ra,
- 2) —NO2,
- 3) —SRb,
- 4) —NRbRb,
- 5) —CN or
- 6) —NRbC(O)Rb;
- Cy is cycloalkyl, heterocyclyl, aryl or heteroaryl;
- t is an integer from 0 to 3;
- n is the integer 1 or 2;
- X is a bond or C(R6);
- and
- L is C(R6), S or N.
100 more elements
Dependencies are inferred from the claim text.