Tri-substituted phenyl derivatives and analogues
AssigneeAstraZeneca AB
InventorsMaria Boije, Jonas Fagerhag, Eva-Lotte Lindstedt Alstermark, Bengt Ohlsson
Life of this patent
Estimating the term…
Abstract
The present invention relates to certain tri-substituted phenyl derivatives and analogues of formula (I), to a process for preparing such compounds, having the utility in clinical conditions associated with insulin resistance, to methods for their therapeutic use and to pharmaceutical compositions containing them.
Claims7
A compound of formula (I)
- 26
- and stereo and optical isomers and racemates thereof as well as pharmaceutically acceptable salts, solvates and prodrug forms thereof, in which formula A is situated in the ortho, meta or para position and represents
- 27
- R is hydrogen;
- —ORa, wherein Ra represents hydrogen, alkyl, aryl or alkylaryl;
- —NRaRb, wherein Ra and Rb are the same or different and Ra is as defined above and Rb represents hydrogen, alkyl, aryl, alkylaryl, cyano, —OH, —Oalkyl, —Oaryl, —Oalkylaryl, —CORc or —SO2Rd, wherein Rc represents hydrogen, alkyl, aryl or alkylaryl and Rd represents alkyl, aryl or alkylaryl;
- R1 is alkyl, aryl, alkene, alkyne, cyano;
- —ORe, wherein Re is alkyl, acyl, aryl or alkylaryl;
- —O—[CH2]u—ORf, wherein Rf represents hydrogen, alkyl, acyl, aryl or alkylaryl and u represents an integer 1-8;
- —OCONRaRc, wherein Ra and Rc are as defined above;
- —SRd, wherein Rd is as defined above;
- —SO2NRaRf, wherein Rf and Ra are as defined above;
- —SO2ORa, wherein Ra is as defined above;
- —COORd, wherein Rd is as defined above;
- R2 is hydrogen, halogen, alkyl, aryl, or alkylaryl,
- R3 and R4 are the same or different and each represents hydrogen, alkyl, aryl, alkylaryl or halogen;
- m is an integer 0-1, preferably m is 1;
- n is an integer 1-6,
- D is situated in the ortho, meta or para position and represents —OSO2Rd, wherein Rd is as defined above;
- —OCONRfRa, wherein Rf and Ra are as defined above;
- —NRcCOORd, wherein Rc and Rd are as defined above;
- —NRcCORa, wherein Rc and Ra are as defined above;
- —NRcRd, wherein Rc and Rd are as defined above;
- —NRcSO2Rd, wherein Rc and Rd are as defined above;
- —NRcCONRaRk, wherein Ra, Rc and Rk are the same or different and each represents hydrogen, alkyl, aryl, or alkylaryl;
- —NRcCSNRaRk, wherein Ra, Rc and Rk are the same or different and each represents hydrogen, alkyl, aryl or alkylaryl;
- —SO2Rd, wherein Rd is as defined above;
- —SORd, wherein Rd is as defined above;
- —SRc, wherein Rc is as defined above;
- —SO2NRaRf, wherein Rf and Ra are as defined above;
- —SO2ORa, wherein Ra is as defined above;
- —CN,
- —CONRcRa, wherein Rc and Ra are as defined above;
- D′ is situated in the ortho, meta or para position and represents hydrogen, alkyl, acyl, aryl, alkylaryl, halogen, —CN, —NO2, 13 NRfRb, wherein Rf and Rb are as defined above;
- —ORf, wherein Rf is as defined above;
- —OSO2Rd, wherein Rd is as defined above;
- alternatively D′ may represent cycloalkyl, CF3, or aryl substituted by Rf;
- D″ is situated in the ortho, meta or para position (preferably D″ is in the ortho position) each D″ independently represents, alkyl, acyl, aryl, alkylaryl, halogen, —CN,
- —NRfRb wherein Rf and Rb are as defined above;
- —ORf, wherein Rf is as defined above;
- and
- —OSO2Rd, wherein Rd is as defined above;
- and
- u is an integer 1 or 2.
A compound of formula I as claimed in any claim from 1 to 4 for use as a medicament.
A pharmaceutical formulation comprising a compound of formula I, as defined in any claim from 1 to 4 and a pharmaceutically acceptable adjuvant, diluent or carrier.
Use of a compound of formula I, as defined in any claim form 1 to 4, in the preparation of a medicament for the treatment or prophylaxis of conditions associated with a patient having reduced sensitivity to insulin.
Dependencies are inferred from the claim text.