Back to results
US 2003/0225072 A1Published application
Opioid receptor active compounds
AssigneeThe Curators of the University of Missouri
InventorsWilliam J. Welsh, Seong Jae Yu, Anil Nair
Life of this patent
Estimating the term…
Abstract
The invention provides compounds of formula I: 1 wherein R1 to R4 and n have any of the meanings defined in the specification and their pharmaceutically acceptable salts. The invention also provides pharmaceutical compositions comprising a compound of formula I, processes for preparing compounds of formula I, intermediates useful for preparing compounds of formula I, and therapeutic methods for treating pain and treating other conditions which involve, for example, binding opioid receptors using compounds of formula I.
Claims84
A compound of formula I:
- 15
- wherein:
- R1 is aryl, Het, (C1-7)alkyl, or (C3-12)cycloalkyl, which (C1-7)alkyl or (C3-12)cycloalkyl are each independently optionally substituted with from 1 to 5 aryl, Het, ORa, halo, NO2, NRaRb, cyano, CONRaRb, CO2Ra, SOmRa, S(O)mNRaRb, or P(═O)(ORa)(Ra);
- R2 is H, (C1-7)alkyl, (C3-12)cycloalkyl, aryl, Het, or a group that includes one or more basic atoms;
- R3 is H, or (C1-7)alkyl;
- each R4 is independently ORa, trifluoromethoxy, trifluoromethyl, halo, NO2, NRaRb, cyano, CONRaRb, CO2Ra, SOmRa, S(O)mNRaRb, P(═O)(ORa)(Ra), (C1-7)alkyl, (C2-7)alkanoyl, (C2-7)alkanoyloxy, or (C3-12)cycloalkyl;
- Ra and Rb are each independently H, (C1-7)alkyl, (C3-12)cycloalkyl, (C2-7)alkanoyl, (C2-7)alkanoyloxy, or aryl, or Ra and Rb together with a nitrogen to which they are attached form a Het;
- wherein any aryl or Het of R1 or R2 is optionally substituted with from 1 to 4 substituents independently selected from ORa, trifluoromethoxy, trifluoromethyl, halo, NO2, NRaRb, cyano, CONRaRb, CO2Ra, SOmRa, S(O)mNRaRb, P(═O)(ORa)(Ra), (C1-7)alkyl, (C2-7)alkanoyl, (C2-7)alkanoyloxy, or (C3-12)cycloalkyl;
- and
- m is 0, 1, or 2;
- n is 0, 1, 2, 3, or 4;
- or a pharmaceutically acceptable salt thereof.
9 more elements
A compound of formula III:
- 17
- wherein:
- R1 is aryl, Het, (C1-7)alkyl, or (C3-12)cycloalkyl, which (C1-7)alkyl or (C3-12)cycloalkyl are each independently optionally substituted with from 1 to 5 aryl, Het, ORa, halo, NO2, NRaRb, cyano, CONRaRb, CO2Ra, SOmRa, S(O)mNRaRb, or P(═O)(ORa)(Ra);
- R2 is H, (C1-7)alkyl, (C3-12)cycloalkyl, aryl, Het, or a group that includes one or more basic atoms;
- R3 is H, or (C1-7)alkyl;
- each R4 is independently ORa, trifluoromethoxy, trifluoromethyl, halo, NO2, NRaRb, cyano, CONRaRb, CO2Ra, SOmRa, S(O)mNRaRb, P(═O)(ORa)(Ra), (C1-7)alkyl, (C2-7)alkanoyl, (C2-7)alkanoyloxy, or (C3-12)cycloalkyl;
- Ra and Rb are each independently H, (C1-7)alkyl, (C3-12)cycloalkyl, (C2-7)alkanoyl, (C2-7)alkanoyloxy, aryl, or Ra and Rb together with a nitrogen to which they are attached form a Het;
- wherein any aryl or Het of R2 is optionally substituted with from 1 to 4 substituents independently selected from ORa, trifluoromethoxy, trifluoromethyl, halo, NO2, NRaRb, cyano, CONRaRb, CO2Ra, SOmRa, S(O)mNRaRb, P(═O)(ORa)(Ra), (C1-7)alkyl, (C2-7)alkanoyl, (C2-7)alkanoyloxy, or (C3-12)cycloalkyl;
- m is 0, 1, or 2;
- and
- n is 0, 1, 2, 3, or 4.
8 more elements
A compound of the formula IV:
- 18
- wherein:
- R2 is H, (C1-7)alkyl, (C3-12)cycloalkyl, aryl, Het, or a group that includes one or more basic atoms;
- R3 is H, or (C1-7)alkyl;
- each R4 is independently ORa, trifluoromethoxy, trifluoromethyl, halo, NO2, NRaRb, cyano, CONRaRb, CO2Ra, SOmRa, S(O)mNRaRb, P(═O)(ORa)(Ra), (C1-7)alkyl, (C2-7)alkanoyl, (C2-7)alkanoyloxy, or (C3-12)cycloalkyl;
- R5, R6, R7, R8, and R9 are each independently H, ORa, trifluoromethoxy, trifluoromethyl, halo, NO2, NRaRb, cyano, CONRaRb, CO2Ra, SOmRa, S(O)mNRaRb, P(═O)(ORa )(Ra), (C1-7)alkyl, (C2-7)alkanoyl, (C2-7)alkanoyloxy, or (C3-12)cycloalkyl;
- Ra and Rb are each independently H, (C1-7)alkyl, (C3-12)cycloalkyl, (C2-7alkanoyl, (C2-7)alkanoyloxy, aryl, or Ra and Rb together with a nitrogen to which they are attached form a Het;
- Rc and Rd are each independently H, (C1-7)alkyl, (C3-12)cycloalkyl, (C2-7)alkanoyl, (C2-7)alkanoyloxy, or aryl;
- wherein any aryl or Het of R2 is optionally substituted with from 1 to 4 substituents independently selected from ORa, trifluoromethoxy, trifluoromethyl, halo, NO2, NRaRb, cyano, CONRaRb, CO2Ra, SOmRa, S(O)mNRaRb, P(═O)(ORa)(Ra), (C1-7)alkyl, (C2-7)alkanoyl, (C2-7)alkanoyloxy, or (C3-12)cycloalkyl;
- m is 0, 1, or 2;
- and
- n is 0, 1, 2, 3, or 4.
9 more elements
Dependencies are inferred from the claim text.