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US 9,802,914 B2Granted
Antifungal compound process
AssigneeViamet Pharmaceuticals, Inc.
InventorsWilliam J. Hoekstra, Christopher M. Yates
Life of this patent
Estimating the term…
Abstract
The present invention relates to a process for preparing compound 1 that is useful as an antifungal agent. In particular, the invention seeks to provide new methodology for preparing compound 1 or 1a and substituted derivatives thereof.
Claims10
A process to prepare compound 1 or 1a, or a mixture thereof;
- or a salt of compound 1 or 1a, or a mixture thereof:
- the process comprising nitromethylating a compound of formula 15:
- to provide a compound of formula 17 or 17a,
- or a mixture thereof;
- and
- converting a compound of formula 17 or 17a,
- or a mixture thereof, to compound 1 or 1a, or a mixture thereof;
- wherein R is halo, —O(C═O)-alkyl, —O(C═O)-substituted alkyl, —O(C═O)-aryl, —O(C═O)-substituted aryl, —O(C═O)—O-alkyl, —O(C═O)—O-substituted alkyl, —O(C═O)—O-aryl, —O(C═O)—O-substituted aryl, —O(SO2)-alkyl, —O(SO2)-substituted alkyl, —O(SO2)-aryl, or —O(SO2)-substituted aryl.
5 more elements
A process to prepare compound 1 or 1a, or a mixture thereof;
- or a salt of compound 1 or 1a, or a mixture thereof:
- the process comprising:
- (i) arylating a compound of formula 15,
- to provide ketone
- (ii) nitromethylating ketone 16,
- to provide nitro-alcohol 18 or 18a,
- or a mixture thereof;
- (iii) reducing nitro-alcohol 18 or 18a,
- or a mixture thereof, to provide amino-alcohol 20 or 20a
- or a mixture thereof;
- and
- (iv) forming the tetrazole of amino-alcohol 20 or 20a,
- or a mixture thereof, to provide compound 1 or 1a,
- or a mixture thereof;
- wherein R is halo, —O(C═O)-alkyl, —O(C═O)-substituted alkyl, —O(C═O)-aryl, —O(C═O)-substituted aryl, —O(C═O)—O-alkyl, —O(C═O)—O-substituted alkyl, —O(C═O)—O-aryl, —O(C═O)—O-substituted aryl, —O(SO2)-alkyl, —O(SO2)-substituted alkyl, —O(SO2)-aryl, or —O(SO2)-substituted aryl.
12 more elements
A process to prepare compound 1 or 1a, or a mixture thereof;
- or a salt of compound 1 or 1a, or a mixture thereof:
- the process comprising:
- (i) arylating a compound of formula 15,
- to provide ketone 16,
- (ii) forming the cyanohydrin of ketone 16,
- to provide nitrile 24 or 24a,
- or a mixture thereof;
- (iii) reducing nitrile 24 or 24a
- or a mixture thereof, to provide amino-alcohol 20 or 20a,
- or a mixture thereof;
- and
- (iv) forming the tetrazole of amino-alcohol 20 or 20a,
- or a mixture thereof, to provide compound 1 or 1a,
- or a mixture thereof;
- wherein R is halo, —O(C═O)-alkyl, —O(C═O)-substituted alkyl, —O(C═O)-aryl, —O(C═O)-substituted aryl, —O(C═O)—O-alkyl, —O(C═O)—O-substituted alkyl, —O(C═O)—O-aryl, —O(C═O)—O-substituted aryl, —O(SO2)-alkyl, —O(SO2)-substituted alkyl, —O(SO2)-aryl, or —O(SO2)-substituted aryl;
- and
- R′ is H or trimethylsilyl.
14 more elements
A process to prepare compound 1 or 1a, or a mixture thereof;
- or a salt of compound 1 or 1a, or a mixture thereof:
- the process comprising:
- cyanating a compound of formula 15,
- to provide a compound of formula 23 or 23a,
- or a mixture thereof;
- and
- converting a compound of formula 23 or 23a,
- or a mixture thereof, to provide compound 1 or 1a,
- or a mixture thereof;
- wherein R is halo, —O(C═O)-alkyl, —O(C═O)-substituted alkyl, —O(C═O)-aryl, —O(C═O)-substituted aryl, —O(C═O)—O-alkyl, —O(C═O)—O-substituted alkyl, —O(C═O)—O-aryl, —O(C═O)—O-substituted aryl, —O(SO2)-alkyl, —O(SO2)-substituted alkyl, —O(SO2)-aryl, or —O(SO2)-substituted aryl;
- and
- R′ is H or trimethylsilyl.
9 more elements
Dependencies are inferred from the claim text.