Drug – bio-affecting and body treating compositions – Preparations characterized by special physical form – Matrices
Reexamination Certificate
2001-04-10
2002-10-01
Dees, Jose′ G. (Department: 1616)
Drug, bio-affecting and body treating compositions
Preparations characterized by special physical form
Matrices
C528S272000, C528S286000
Reexamination Certificate
active
06458385
ABSTRACT:
BACKGROUND OF THE INVENTION
Since Carothers early work in the 1920s and 1930s, aromatic polyester 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.
Only recently has there 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.
Thus it is an object of the present invention to provide crosslinked aliphatic polyoxaamides (which includes polyoxaesteramides) and blends thereof with other polymers that may be used in surgical devices such as sutures, molded devices, drug delivery matrices, coatings, lubricants and the like.
SUMMARY OF THE INVENTION
We have discovered a new class of synthetic crosslinked polyoxaamides and blends thereof with other polymers that may be used to produce a variety of useful products including surgical devices such molded devices, drug delivery matrices, coatings, lubricants and the like. The crosslinked polyoxaamide polymers of the present invention are polymers comprising a first divalent repeating unit of formula I:
[X—C(O)—C(R
1
)(R
2
)—O—(R
3
)—O—C(R
1
)(R
2
)—C(O)—] I
and a second repeating unit selected from the group of formulas consisting of:
[—Y—R
17
—]
T
, II
[—O—R
5
—C(O)—]
B
, III
([—O—R
9
—C(O)]
P
—O—)
L
G XI
and combinations thereof, wherein X and Y are selected from the group consisting of —O— and —N(R)—, provided that X and Y cannot both be —O—; R, R
1
and R
2
are independently selected from the group consisting of hydrogen and an alkyl group containing 1 to 8 carbon atoms; R
3
is selected from the group consisting of an alkylene unit and 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 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 in the range of from 2 to about 12; R
17
is a alkylene unit containing from 2 to 8 carbon atoms which may have substituted therein an internal ether oxygen, an internal —N(R
18
)— or an internal —C(O)—N(R
21
)—; T is an integer in the range of from 1 to about 2,000 and preferably is in the range of from 1 to about 1,000; R
18
and R
21
are independently selected from the group consisting of hydrogen and an alkyl group containing 1 to 8 carbon atoms; R
5
and R
9
are 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
)
K
—C(O)—CH
2
—; R
6
and R
7
are independently selected from the group consisting of hydrogen and an alkyl containing from 1 to 8 carbon atoms; R
8
is selected from the group consisting of hydrogen and methyl; F and K are independently selected 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 100,000 and more 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 200,000 and more preferably less than 40,000; G represents the residue minus from 1 to L hydrogen atoms from the hydroxyl groups of an alcohol previously containing from 1 to about 200 hydroxyl groups; and L is an integer from about 1 to about 200; which have been crosslinked.
Additionally, the present invention describes a prepolymer comprising an aliphatic polyoxaamide chemically linked to at least one polymerizable region.
DETAILED DESCRIPTION OF THE INVENTION
The aliphatic polyoxaamides (which also includes polyoxaesteramides that are within the scope of the present invention) of the present invention are the reaction product of 1) an aliphatic polyoxydicarboxylic acid and a diamine or amino alcohol optionally containing one of the following compounds: a diol (or polydiol), a lactone (or lactone oligomer), a coupling agent or combination thereof. Suitable aliphatic alpha-oxydicarboxylic acids (or oxadicarboxylic acids) for use in the present invention 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, R
1
and R
2
are independently selected from the group consisting of hydrogen and 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 0 to about 2,000 and preferably 1 to about 12, 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 in the range of from 2 to 12. These aliphatic alpha-oxydicarboxylic acids may be formed by reacting a diol or polydiol with an alpha-halocarboxylic acid such bromoacetic acid or chloroacetic acid under suitable conditions.
In some instances the corresponding mono or diester of the aliphatic alpha-oxydicarboxylic acids of formula V may be used.
Suitable amino alcohols, diamines, diols or polydiols for use in the present invention have repeating units with up to 8 carbon atoms having the formulas:
H[—(N(R
12
)—R
13
—)
U
]OH VIA
H[—(N(R
14
)—R
15
—)
V
N(R
16
) VIB
H[—(O—R
4
—)
A
]OH, VIC
H[—(O—R
19
—)
Z
]N(R
20
)H, VID
w
Bezwada Rao S.
Jamiolkowski Dennis D.
Dees Jose′ G.
Ethicon Inc.
George Konata M.
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