Synthesis and application of microbubble-forming compounds
AssigneeCalifornia Institute of Technology
InventorsVanessa M. Marx, Robert H. Grubbs
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Abstract
The present disclosure is directed to fatty-acid glycerol ester derivative compounds containing a targeting bisphosphonate group. The disclosure further include pharmaceutical or biomedical compositions comprising these compounds, and methods of using these compounds and compositions forming microbubbles. The microbubbles have affinity for metal-containing, especially calcium-containing, bodies and/or biological targets. In certain embodiments, these compositions are useful for providing targeted placement of microbubbles capable of cavitation on application of high frequency energy.
Claims9
A pharmaceutical or biomedical composition comprising one or more compounds of the formula selected from the group consisting of formula (I), formula (Ia), formula (II), formula (III), formula (IV) and formula (V):
- wherein:
- each n is independently selected from 0-7;
- each m is independently selected from 0-26;
- each p is independently selected from 7-26;
- each q is independently selected from 1-90;
- each R1 is independently selected from the group consisting of:
- hydrogen, C1-C26 alkyl, C1-C26 substituted alkyl, C1-C26 alkenyl, C1-C26 substituted alkenyl, C1-C26 alkynyl, C1-C26 substituted alkynyl, C1-C26 alkyl aryl, C1-C26 substituted alkyl aryl, C1-C26 alkenyl aryl, C1-C26 substituted alkenyl aryl, C1-C26 alkynyl aryl, C1-C26 substituted alkynyl aryl;
- each R2 is independently selected from the group consisting of:
- hydrogen, C1-C26 alkyl, C1-C26 substituted alkyl, C1-C26 alkenyl, C1-C26 substituted alkenyl, C1-C26 alkynyl, C1-C26 substituted alkynyl, C1-C26 alkyl aryl, C1-C26 substituted alkyl aryl, C1-C26 alkenyl aryl, C1-C26 substituted alkenyl aryl, C1-C26 alkynyl aryl, C1-C26 substituted alkynyl aryl, C3-C8 cycloalkyl, C3-C8 substituted cycloalkyl, C3-C8 aryl, C3-C8 substituted aryl, C3-C8 heterocycloalkyl, C3-C8 substituted heterocycloalkyl, C3-C8 heteroaryl, C3-C8 substituted heteroaryl, acyl, aminoacyl, thioacyl, aminocarbonyl, aminoacyl carbonyloxy, aminothiocarbonyl, aminosulfonyl, amidino, substituted sulfonyl, substituted sulfinyl, carboxy ester, phthalimido, SO3H and PO3H;
- C is selected from the group consisting of:
- B is selected from the group consisting of:
- a covalent bond, ethylene glycol, and polyethylene glycol;
- A is selected from the group consisting of:
- a covalent bond, acyl, acylamino, aminoacyl, acyloxy, thioacyl, aminocarbonyl, aminoacyl carbonyloxy, aminothiocarbonyl, aminocarbonylamino, aminothiocarbonylamino, aminocarbonyloxy, aminosulfonyloxy, aminosulfonylamino, aminosulfonyl, amidino, and carboxy ester, wherein any of these functional groups listed for A may be covalently bonded on either side to the
- moiety;
- Y is selected from the group consisting of:
- a covalent bond, acyl, acylamino, aminoacyl, acyloxy, thioacyl, aminocarbonyl, aminoacyl carbonyloxy, aminothiocarbonyl, aminocarbonylamino, aminothiocarbonylamino, aminocarbonyloxy, aminosulfonyloxy, aminosulfonylamino, aminosulfonyl, amidino, and carboxy ester, wherein any of these functional groups listed for A may be covalently bonded on either side to either one of the
- moieties;
- X is selected from the group consisting of:
- hydrogen, silyl, acyl, aminoacyl, thioacyl, aminocarbonyl, aminoacyl carbonyloxy, aminothiocarbonyl, aminosulfonyl, amidino, substituted sulfonyl, substituted sulfinyl, carboxy ester, phthalimido, SO3H and PO3H;
- W is selected from the group consisting of:
- O, NR2, and S;
- Z is selected from the group consisting of:
- a covalent bond, CH2, O, NR2, and S;
- M is selected from the group consisting of:
- a covalent bond, CH2—CH2, CH2—CH2—Z, CH2—Z and CH2;
- or a tautomer and/or a pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.