Fatty alcohol drug conjugates
AssigneeLuitpold Pharmaceuticals, Inc.
InventorsCharles S. Swindell, Glenn J. Fegley
Life of this patent
Estimating the term…
Abstract
The invention provides conjugates of fatty alcohols and pharmaceutical agents useful in treating cancer, viruses, psychiatric disorders. Compositions, pharmaceutical preparations, and methods of preparation of the fatty alcohols-pharmaceutical agent conjugates are provided.
Claims136
A compound of the formula:
- 65
- wherein r is a C8-C26 fatty group of a fatty alcohol ROH and X is a pharmaceutical agent moiety of a pharmaceutical agent XOH.
A compound of the formula:
- 69
- wherein R is a C8-C26 fatty group of a fatty alcohol ROH, X is a pharmaceutical agent moiety of a pharmaceutical agent XZH, wherein Z is O, a primary amino group, or a secondary amino group, and R′ is H, an ion, or a protecting group.
A compound of the formula:
- 70
- wherein R is a C8-C26 fatty group of a fatty alcohol ROH and X is a pharmaceutical agent moiety of a pharmaceutical agent HNR″X, wherein R″ is H, an alkyl group, an alkenyl group, an alkynyl group, or an aryl group.
A compound of the formula:
- 71
- wherein R is a C8-C26 fatty group of a fatty alcohol ROH and X is a pharmaceutical agent moiety of a pharmaceutical agent XC(O)OH.
A compound of the formula:
- 72
- wherein R is a C8-C26 fatty group of a fatty alcohol ROH and X is a pharmaceutical agent moiety of a pharmaceutical agent XNH2.
A compound of the formula:
- 73
- wherein R is a C8-C26 fatty group of a fatty alcohol ROH and T is a leaving group.
A compound of the formula:
- 74
- wherein R is a C8-C26 group of a fatty alcohol ROH, R′ is H, an ion, a protecting group, or a pharmaceutical agent, Y is a protecting group, and T is a leaving group.
A pharmaceutical preparation comprising a compound of the formula
- 75
- wherein R is a C8-C26 fatty group of a fatty alcohol ROH, and X is a pharmaceutical agent moiety of the pharmaceutical agent XOH, and a pharmaceutically acceptable carrier.
A pharmaceutical preparation comprising a compound of the formula:
- 77
- wherein R is a C8-C26 fatty group of a fatty alcohol ROH, X is a pharmaceutical agent moiety of a pharmaceutical agent XZH, wherein Z is O, a primary amino group, or a secondary amino group, and R′ is H, an ion, or a protecting group, and a pharmaceutically acceptable carrier.
A pharmaceutical preparation comprising a compound of the formula:
- 78
- wherein R is a C8-C26 fatty group of a fatty alcohol ROH and X is a pharmaceutical agent moiety of a pharmaceutical agent HNR″X, wherein R″ is H, an alkyl group, or an aryl group and a pharmaceutically acceptable carrier.
A pharmaceutical preparation comprising a compound of the formula:
- 79
- wherein R is a C8-C26 fatty group of a fatty alcohol ROH and X is a pharmaceutical agent moiety of a pharmaceutical agent XC(O)OH and a pharmaceutically acceptable carrier.
A pharmaceutical preparation comprising a compound of the formula:
- 80
- wherein R is a C8-C26 fatty group of a fatty alcohol ROH and X is a pharmaceutical agent moiety of a pharmaceutical agent XNH2 and a pharmaceutically acceptable carrier.
The pharmaceutical preparation of claim 83, wherein the fatty alcohol ROH has a carbon structure that is the same as a carbon structure of a fatty acid selected from myristic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, vaccenic acid, linoleic acid, linolenic acid, arachidonic acid, eicosapentaenoic acid, docosenoic acid, docosatetraenoic acid, docosapentaenoic acid, docosahexaenoic acid, and nervonic acid.
A method of making a compound of the formula:
- 81
- comprising reacting an intermediate of the formula ROC(O)T with a pharmaceutical agent of the formula XOH for a time sufficient to form the compound wherein R is a C8-C26 fatty group of a fatty alcohol ROH, and X is a pharmaceutical agent moiety of the pharmaceutical agent of the formula XOH.
A method of making a compound of the formula:
- 82
- comprising reacting an intermediate of the formula:
- 83
- with a pharmaceutical agent XZH for a time sufficient to form the compound wherein R is a C8-C26 fatty group of a fatty alcohol ROH, X is a pharmaceutical agent moiety of the pharmaceutical agent XZH, wherein Z is O, a primary amino group, or a secondary amino group, and R′ is H, an ion, a protecting group or a second pharmaceutical agent.
A method of making a compound of the formula:
- 84
- comprising reacting an intermediate of the formula ROC(O)T with a pharmaceutical agent of the formula HNR″X for a time sufficient to form the compound wherein R is a C8-C26 fatty group of a fatty alcohol ROH, X is a pharmaceutical agent moiety of the pharmaceutical agent of the formula HNR″X, R″ is a H, an alkyl group, or an aryl group.
A method of making a compound of the formula:
- 85
- comprising:
- derivatizing a pharmaceutical agent of the formula XC(O)OH with a leaving group to form an intermediate;
- and
- reacting the intermediate with a fatty alcohol of the formula ROH for a time sufficient to form the compound wherein R is a C8-C26 fatty group of the fatty alcohol, and X is a pharmaceutical agent moiety of the pharmaceutical agent of the formula XC(O)OH.
A method of treating a disorder comprising administering to a subject in need of such treatment a pharmaceutical preparation comprising a compound of the formula:
- 86
- and a pharmaceutically acceptable carrier wherein R is a C8-C26 fatty group of a fatty alcohol ROH, and X is a pharmaceutical agent moiety of the pharmaceutical agent XOH.
A method of treating a disorder comprising administering to a subject in need of such treatment a pharmaceutical preparation comprising a compound of the formula:
- 90
- and a pharmaceutically acceptable carrier wherein R is a C8-C26 fatty group of a fatty alcohol ROH, X is a pharmaceutical agent moiety of a pharmaceutical agent XZH, wherein Z is O, a primary amino group, or a secondary amino group, and R′ is H, an ion, or a protecting group.
A method of treating a disorder comprising administering to a subject in need of such treatment a pharmaceutical composition comprising a compound of the formula:
- 91
- and a pharmaceutically acceptable carrier wherein R is a C8-C26 fatty group of a fatty alcohol ROH and X is a pharmaceutical agent moiety of a pharmaceutical agent HNR″X, wherein R″ is H, an alkyl group, or an aryl group.
A method of treating a disorder comprising administering to a subject in need of such treatment a pharmaceutical composition comprising a compound of the formula:
- 92
- and a pharmaceutically acceptable carrier wherein R is a C8-C26 fatty group of a fatty alcohol ROH and X is a pharmaceutical agent moiety of a pharmaceutical agent XC(O)OH and a pharmaceutically acceptable carrier.
A method of treating a disorder comprising administering to a subject in need of such treatment a pharmaceutical composition comprising a compound of the formula:
- 93
- and a pharmaceutically acceptable carrier wherein R is a C8-C26 fatty group of a fatty alcohol ROH and X is a pharmaceutical agent moiety of a pharmaceutical agent XNH2 and a pharmaceutically acceptable carrier.
Dependencies are inferred from the claim text.