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US 7,402,673 B2Granted
Diamine β2 adrenergic receptor agonists
AssigneeTheravance, Inc.
InventorMartin S. Linsell
Life of this patent
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Abstract
The invention provides novel β2 adrenergic receptor agonist compounds. The invention also provides pharmaceutical compositions comprising such compounds, methods of using such compounds to treat diseases associated with β2 adrenergic receptor activity, and processes and intermediates useful for preparing such compounds.
Claims24
A compound of formula (I):
- wherein:
- each of R1, R2, R3, and R4 is independently selected from hydrogen, hydroxy, amino, halo, —CH2OH and —NHCHO, or R1 and R2 taken together are selected from —NHC(═O)CH═CH—, —CH═CHC(═O)NH—, —NHC(═O)S—;
- and —SC(═O)NH—;
- R5 is selected from hydrogen and —NRaRb, wherein Ra and Rb are each independently hydrogen or C1-3alkyl;
- n is an integer of from 2 to 6;
- m is an integer of from 0 to 5;
- and
- each of R6, R7, R8, R9, and R10 is independently hydrogen or C1-6alkyl;
- provided that when m is 0, R5 is hydrogen;
- or a pharmaceutically-acceptable salt or solvate or stereoisomer thereof.
7 more elements
A compound having the chemical name 8-hydroxy-5-[(R)-1-hydroxy-2-(6-phenethylamino-hexylamino)ethyl]-quinolin-2-one;
- or a pharmaceutically-acceptable salt or solvate or stereoisomer thereof.
A process for preparing a compound of formula (I),
- wherein:
- each of R1, R2, R3, and R4 is independently selected from hydrogen, hydroxy, amino, halo, —CH2OH and —NHCHO, or R1 and R2 taken together are selected from —NHC(═O)CH═CH—, —CH═CHC(═O)NH—, —NHC(═O)S—;
- and —SC(═O)NH—;
- R5 selected from hydrogen and —NRaRb, wherein Ra and Rb are each independently hydrogen or C1-3alkyl;
- n is an integer of from 2 to 6;
- m is an integer of from 0 to 5;
- and
- each of R6, R7, R8, R9, and R10 is independently hydrogen or C1-6alkyl;
- provided that when m is 0, R5 is hydrogen;
- or a pharmaceutically-acceptable salt or stereoisomer thereof, the process comprising:
- (a) reacting a compound of formula (III):
- wherein:
- P1 is a hydroxy-protecting group, L is a leaving group, each of R1a, R2a, R3a, and R4a is independently selected from hydrogen, hydroxy, amino, halo, —CH2OH —NHCHO, and —OP2, wherein P2 is a hydroxy-protecting group, or R1a and R2a taken together are selected from —NHC(═O)CH═CH—, —CH═CHC(═O)NH—, —NHC(═O)S—;
- and —SC(═O)NH—;
- with a compound of formula (IV):
- wherein R11 is hydrogen or P3 wherein P3 is an amino-protecting group, to provide a compound of formula (V):
- (b) removing the protecting group P1 to provide a compound of formula (VI):
- and
- (c) when any of R1a, R2a, R3a, or R4a is —OP2 or when R11 is P3, removing the protecting groups P2 and P3, if present to provide a compound of formula (I), or a salt or stereoisomer thereof.
16 more elements
Dependencies are inferred from the claim text.