US 8,524,259 B2Granted

Systems and methods for delivery of materials

AssigneeLandec Corporation

InventorsDavid D. Taft, Steven Bitler, Qiang Zheng, Stelios Tzannis, Adam Bell, Wei-Guo Dai, Sandra N. Ottensmann, Natarajan Balachander

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Abstract

Systems and methods for delivering release materials, for example drugs and other bioactive materials. Crystalline polymeric systems, referred to as CYC carriers, are associated with the release materials, through chemical bonding or through physical association. The crystallinity of the CYC carriers results from the presence of crystallizable side chains, for example long chain n-alkyl moieties, which results in relatively low and sharp melting temperatures. One class of CYC carriers, referred to as CYSC polymers, have a majority of the crystallizable side chains pendant from the polymer backbone. Another class of CYC carriers referred to as ECC polymers, have a majority of the crystallizable side chains attached to terminal units of the polymer backbone. The ECC polymers can for example be obtained by modification of PLGA polymers. The CYC carriers in another class of non-polymeric. Some CYC carriers, referred to as CYC assemblies, have enhanced crystallinity as a result of the physical association of crystallizable moieties which are present in different types of molecule, for example between a polymer containing crystallizable moieties and a monomer containing crystallizable moieties. For some uses, particularly the delivery of drugs, a bioerodable CYC carrier is preferably used.

Claims21

Dependent claims

A composition which comprises an end cap crystalline (ECC) polymer and a release material associated with the ECC polymer, the release material being (1) one or more bioactive materials which are useful in agricultural applications and which are selected from the group consisting of fertilizers, biocides, insecticides and fungicides or (2) one or more additives which are useful in personal care compositions and which are selected from the group consisting of UV absorbers, fragrances, biocides, antimicrobial agents, germicides, antioxidants, preservatives, disinfectants, enzymes, nutrients and minerals, wherein the ECC polymer

(A) comprises a plurality of polymeric molecules each of which consists essentially of
(i) a polymer backbone which comprises a plurality of repeating units having the formula
—CF1F2—CO—O— (1)
wherein
F1 is hydrogen and F2 is hydrogen or methyl, the repeating units being the same or different, and
(ii) at least one terminal unit which has the formula
-b-Cy (2)
the Cy moieties in said terminal units providing at least 50% by weight of the Cy moieties in the polymeric molecules, and
Cy being a moiety which is (a) associated with other Cy moieties to provide the ECC polymer with crystallinity and (b) is a moiety which consists of (i) an n-alkyl moiety containing 14-50 carbon atoms, or (ii) a moiety which consists of an n-alkyl moiety containing 14-50 carbon atoms and a polyoxyalkylene moiety, and
b is a bond or a moiety which has a valence of at least 2, which links the Cy moiety to the polymer backbone and which optionally contains additional Cy moieties;
wherein each terminal unit having formula (2) is a moiety selected from the group consisting of
(2A) moieties (i) in which b is a bond, (ii) which have the formula —Cy and (iii) which are directly linked to the terminal —CO—O—moiety of one of the repeating units having formula (1),
(2B) moieties (i) in which b is a moiety having the formula —O—CO—, (ii) which have the formula
—O—CO-Cy
and (iii) which are directly linked to the terminal —CF1F2—moiety of one of the repeating units having formula (1), and
(2C) moieties (i) in which b is a moiety having the formula —Rpbalc—O—CO—, (ii) which have the formula
—Rpbalc—O—CO-Cy
where Rpbalc is the residue of a polyol of and (iii) which are directly linked to the terminal —CO—O—moiety of one of the repeating units having formula (1);
and
(B) has a crystalline melting temperature, Tp, of at least 0° C. and a heat of fusion, ΔH, of at least 3 J/g which result from association of the Cy moieties, Tp and ΔH being measured on a differential scanning calorimeter.

17 more elements

(1) comprises a plurality of polymeric molecules each of which consists essentially of
(i) a polymer backbone which comprises a plurality of repeating units having the formula
—CF1F2—CO—O— (1)
wherein
F1 is hydrogen and F2 is hydrogen or methyl, the repeating units being the same or different, and
(ii) at least one terminal unit which has the formula
-b-Cy (2)
the Cy moieties in said terminal units providing at least 50% by weight of the Cy moieties in the polymeric molecules, and
Cy being a moiety which is associated with other Cy moieties to provide the ECC polymer with crystallinity and being a moiety which consists of (1) an n-alkyl moiety containing 18-24 carbon atoms or (2) an n-alkyl moiety containing 18-24 carbon atoms and a polyoxyalkylene unit, and
b being a bond or a moiety which has a valence of at least 2 and which links the Cy moiety to the polymer backbone, and which optionally contains additional Cy moieties;
wherein each terminal unit having formula (2) is a moiety selected from the group consisting of
(2A) moieties (i) in which b is a bond, (ii) which have the formula -Cy and (iii) which are directly linked to the terminal —CO—O—moiety of one of the repeating units having formula (1),
(2B) moieties (i) in which b is a moiety having the formula —O—CO—, (ii) which have the formula
—O—CO-Cy
and (iii) which are directly linked to the terminal —CF1 F2 —moiety of one of the repeating units having formula (1), and
(2C) moieties (i) in which b is a moiety having the formula —Rpbalc—O—CO —, (ii) which have the formula
—Rpbalc—O—CO-Cy
where Rpbalc is i the residue of a polyol, and (iii) which are directly linked to the terminal —CO—O—moiety of one of the repeating units having formula (1), and
(B) has a crystalline melting temperature, Tp, of at least 0° C. and a heat of fusion, ΔH, of at least 3 J/g which result from association of the Cy moieties, Tp and ΔH being measured on a differential scanning calorimeter.

16 more elements

Dependencies are inferred from the claim text.

Facts

Application: 12/746,178Filed 3 Dec 2008
Published: US 2011/0009571 A113 Jan 2011
Granted: 3 Sep 2013
Term ends: Not estimatedThe source records don’t support an estimate.

Classification7 codes

A61K 9/0024
Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in…
A61K 9/0019
Galenical forms characterised by the site of application: injectable compositions; Intramuscular, intravenous, arterial, subcutaneous…
A61K 9/146
Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried,…: with…
A61P 25/18
Drugs for disorders of the nervous system: antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia