Drug – bio-affecting and body treating compositions – Designated organic nonactive ingredient containing other... – Solid synthetic organic polymer
Reexamination Certificate
1999-08-17
2002-06-11
Webman, Edward J. (Department: 1617)
Drug, bio-affecting and body treating compositions
Designated organic nonactive ingredient containing other...
Solid synthetic organic polymer
C525S437000, C525S438000, C525S408000
Reexamination Certificate
active
06403655
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a method of preventing adhesions with bioabsorbable polymers, copolymers and blends thereof.
BACKGROUND OF THE INVENTION
Since Carothers early work in the 1920s and 1930s, aromatic polyesters particularly poly(ethylene terephthalate) have become the most commercial important polyesters. The usefulness of these polymers is intimately linked to the stiffening action of the p-phenylene group in the polymer chain. The presence of the p-phenylene group in the backbone of the polymer chain leads to high melting points and good mechanical properties especially for fibers, films and some molded products. In fact poly(ethylene terephthalate) has become the polymer of choice for many common consumer products, such as one and two liter soft drink containers.
Several related polyester resins have been described in U.S. Pat. Nos. 4,440,922, 4,552,948 and 4,963,641 which seek to improve upon the properties of poly(ethylene terephthalate) by replacing terephthalic acid with other related dicarboxylic acids which contain phenylene groups. These polymers are generally designed to reduce the gas permeability of aromatic polyesters.
Other aromatic polyesters have also been developed for specialty applications such as radiation stable bioabsorbable materials. U.S. Pat. Nos. 4,510,295, 4,546,152 and 4,689,424 describe radiation sterilizable aromatic polyesters which can be used to make sutures and the like. These polymers, like poly(ethylene terephthalate), have phenylene groups in the backbone of the polymers.
However, less research has been reported on aliphatic polyesters. After Carothers initial work on polyesters, aliphatic polyesters were generally ignored because it was believed that these materials had low melting points and high solubilities. The only aliphatic polyesters that have been extensively studied are polylactones such as polylactide, polyglycolide, poly(p-dioxanone) and polycaprolactone. These aliphatic polylactones have been used primarily for bioabsorbable surgical sutures and surgical devices such as staples. Although polylactones have proven to be useful in many applications they do not meet all the needs of the medical community. For example films of polylactones do not readily transmit water vapor, therefore, are not ideally suited for use as bandages where the transmission of water vapor would be desired.
Recently there has been renewed interest in non-lactone aliphatic polyesters. U.S. Pat. No. 5,349,028 describes the formation of very simple aliphatic polyesters based on the reaction of a diol with a dicarboxylic acid to form prepolymer chains that are then coupled together. These polyesters are being promoted for use in fibers and molded articles because these polyesters are biodegradable after they are buried, such as in a landfill. However, these materials are not disclosed as being suitable for use in surgical devices.
To address the deficiencies in the polymers described in the prior art, we invented a new class of polymers which are disclosed in U.S. Pat. Nos. 5,464,929; 5,595,751; 5,597,579; 5,607,687; 5,618,552; 5,620,698; 5,645,850; 5,648,088; 5,698,213; and 5,700,583 (all of which are hereby incorporated by reference). This new class of polymers is hydrolyzable and suitable for a variety of uses including medical applications. To further broaden the possible uses for these polymers, we are disclosing and claiming herein, copolymers of the polyoxaamides (which includes polyoxaesteramides) and blends thereof with other polymers with modified hydrolysis profiles. These polymers may be used in industrial and consumer applications where biodegradable polymers are desirable, as well as, in medical devices.
SUMMARY OF THE INVENTION
We have discovered a method of preventing adhesion formation between tissues in an animal comprising placing a sterile adhesion prevention barrier between the tissues of the animal where the adhesion is to be prevented wherein the sterile adhesion prevention barriers made from a polymer, copolymer or blends thereof of a polyoxaester copolymer having a first divalent repeating unit of formula IA:
[—O—C(O)—C(R
1
)(R
2
) —O—R
3
—O—C(R′
1
)(R′
2
)—C(O)—] IA
and a second repeating unit selected from the group of formulas consisting of:
[—O—R
4
—]
A
, II
[—O—R
5
—C(O)—]
B
, III
([—O—R
5
—C(O)]
P
—O—)
l
G XI
and combinations thereof, wherein R
1
, R′
1
, R
2
and R′
2
are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms; R
3
is an alkylene unit containing from 2 to 12 carbon atoms or is an oxyalkylene group of the following formula:
—[(CH
2
)
C
—O—]
D
—(CH
2
)
E
— IV
wherein C is an integer in the range of from 2 to about 5, D is an integer in the range of from about 0 to about. 2,000, and E is an integer in the range of from about 2 to about 5, except when D is zero, in which case E will be an integer from 2 to 12; R
4
is an alkylene unit containing from 2 to 8 carbon atoms ; A is an integer in the range of from 1 to 2,000; R
5
is selected from the group consisting of —C(R
6
)(R
7
)—, —(CH
2
)
3
—O—, —CH
2
—CH
2
—O—CH
2
—, —CR
8
H—CH
2
—, —(CH
2
)
5
—, —(CH
2
)
F
—O—C(O)— and —(CH
2
)
F
—C(O)—CH
2
—; R
6
and R
7
are independently hydrogen or an alkyl containing from 1 to 8 carbon atoms; R
8
is hydrogen or methyl; F is an integer in the range of from 2 to 6; B is an integer in the range of from 1 to n such that the number average molecular weight of formula III is less than about 200,000, preferably less than about 100,000 and most preferably less than 40,000; P is an integer in the range of from 1 to m such that the number average molecular weight of formula XI is less than about 1,000,000, preferably less than about 200,000 and most preferably less than 40,000; G represents the residue minus from 1 to L hydrogen atoms from the hydroxyl group of an alcohol previously containing from 1 to about 200 hydroxyl groups; and L is an integer from about 1 to about 200.
In another embodiment of the present invention the method of preventing adhesion formation between tissues described above may utilize a barriers made from a polymer, copolymer or blends thereof of a polyoxaester copolymer that additionally contains a third repeating unit of the formula:
[—O—C(O)—R
30
—C(O)—] IB
wherein R
30
is an alkylene, arylene, arylalkylene, substituted alkylene, substituted arylene and substituted alkylarylene provided that R
30
cannot be —[C(R
1
)(R
2
)]
1-2
—O—(R
3
) —O—[C(R′
1
)(R′
2
)]
1-2
—.
DETAILED DESCRIPTION OF THE INVENTION
The aliphatic polyoxaesters of the present invention are the reaction product of 1) an aliphatic polyoxycarboxylic acid; and 2) at least one of the following compounds: a diol (or polydiol), a lactone (or lactone oligomer), a coupling agent or combination thereof and may optionally contain a dicarboxylic acid. For the purpose of this application aliphatic shall mean an organic compound having a straight, branched, or cyclic arrangement of carbon atoms (i.e. alkanes, olefins, cycloalkanes, cycloolefins and alkynes).
Suitable aliphatic poly-oxycarboxylic acids for use in the present invention are alpha, omega-dicarboxy polyoxy compounds generally have the following formula:
HO—C(O)—C(R
1
)(R
2
)—O—R
3
—O—C(R′
1
)(R′
2
)—C(O)—OH V
wherein R
1
, R′
1
, R
2
and R′
2
are independently selected from the group consisting of hydrogen or an alkyl group containing from 1 to 8 carbon atoms and R
3
is an alkylene containing from 2 to 12 carbon atoms or is an oxyalkylene group of the following formula:
—[(CH
2
)
C
—O—]
D
—(CH
2
)
E
— IV
wherein C is an integer in the range of from about 2 to about 5, D is an integer in the range of-from about 0 to about 2,000 and preferably from 0 to 12, and E is an integer in the range of from about 2 to about 5. These polyoxy aliphatic alpha-omega dicarboxylic acids may be formed by rea
Bezwada Rao S.
Jamiolkowski Dennis D.
Ethicon Inc.
Webman Edward J.
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