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US 2016/0107991 A1Published application
Processes and intermediates for preparing indole pharmaceuticals
AssigneeIndiana University Research and Technology Corporation
InventorJames R. MCCARTHY
Life of this patent
Estimating the term…
Abstract
The invention described herein pertains to processes and intermediates for preparing indole containing pharmaceuticals, particularly to processes and intermediates for preparing selective estrogen receptor modulators, such as bazedoxifene.
Claims28
A process for preparing a compound of the formula
- or a pharmaceutically acceptable salt thereof,
- (d) contacting a compound of the formula
- with an acid;
- or
- (c) contacting a first compound of the formula
- with a second compound of the formula
- or a salt thereof, and a base;
- or
- (b) contacting a first compound of the formula
- or a salt thereof, with a reagent capable of converting the hydroxyl group into a leaving group to form a second compound of the formula
- or a salt thereof, where L is the leaving group;
- or
- (a) contacting a first compound of the formula
- with a second compound of the formula
- Ar2—NHNH2
- or a salt thereof;
- or
- a combination of any of the foregoing steps;
- wherein
- Ar1 and Ar2 are each aryl, each of which is independently optionally substituted;
- Ar3 is a group of the formula
- wherein n is 2, 3, 4, or 5;
- and each RN is independently selected from hydrogen, alkyl, heteroalkyl, arylalkyl, and heteroarylalkyl, each of which is optionally substituted, or both RN and the attached nitrogen are taken together to form a cycloheteroalkyl;
- RA is hydrogen, or optionally substituted alkyl or optionally substituted arylalkyl;
- RB is hydrogen, or optionally substituted alkyl or optionally substituted arylalkyl;
- and
- R2 is hydrogen, or represents one or more optional substituents.
24 more elements
-8. (canceled)
(canceled)
(canceled)
-19. (canceled)
(canceled)
-26. (canceled)
-31. (canceled)
-39. (canceled)
A compound of the formula
- or a salt thereof, wherein
- Ar1 and Ar2 are each aryl, each of which is independently optionally substituted;
- and
- RA is hydrogen, optionally substituted alkyl, or optionally substituted arylalkyl.
1 more element
A compound of the formula
- or a salt thereof, wherein
- Ar1 and Ar2 are each aryl, each of which is independently optionally substituted;
- Ar3 is a group of the formula
- wherein n is 2, 3, 4, or 5;
- and each RN is independently selected from hydrogen, alkyl, heteroalkyl, arylalkyl, and heteroarylalkyl, each of which is optionally substituted, or both RN and the attached nitrogen are taken together to form a cycloheteroalkyl;
- RA is hydrogen, optionally substituted alkyl, or optionally substituted arylalkyl;
- and
- RB is hydrogen, optionally substituted alkyl, or optionally substituted arylalkyl.
5 more elements
Dependencies are inferred from the claim text.