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US 2002/0176844 A1Published application
Bioerodible polyorthoesters containing hydrogen bonding groups
OwnerSteven Y. Ng, Jorge Hellerinventors
Life of this patent
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Abstract
Bioerodible polyorthoesters useful as orthopedic implants or vehicles for the sustained delivery of pharmaceutical, cosmetic and agricultural agents contain hydrogen bonding groups and α-hydroxy acid-containing groups.
Claims35
A polyorthoester of formula I:
- 14
- where:
- R* is a C1-4 alkyl;
- n is an integer of at least 5;
- and
- A is R1, R2, R3, or R4, where
- R1 is:
- 15
- where:
- p is an integer of to 20;
- R5 is hydrogen or C1-4 alkyl;
- and
- R is:
- 16
- where:
- s is an integer of 1 to 30;
- t is an integer of 2 to 200;
- and
- R7 is hydrogen or C1-4 alkyl;
- R2is:
- 17
- where:
- x is an integer of 0 to 30;
- y is an integer of 2 to 200;
- R8 is hydrogen or C1-4 alkyl;
- R9 and R10 are independently C1-12 alkylene;
- R11 is hydrogen or C1-6 alkyl and R12 is C1-6 alkyl;
- or R11 and R12 together are C3-10 alkylene;
- and
- R4 is a diol containing at least one functional group independently selected from amide, imide, urea, and urethane groups;
- in which at least 0.1 mol % of the A units are R1, and at least 0.1 mol % of the A units are R4.
28 more elements
A process of preparing a polyorthoester of formula I:
- 18
- where:
- R* is a C1-4 alkyl;
- n is an integer of at least 5;
- and
- A is R1, R2, R3, or R4, where
- R1 is:
- 19
- where:
- p is an integer of 1 to 20;
- R5 is hydrogen or C1-4 alkyl;
- and
- R6 is:
- 20
- where:
- s is an integer of 0 to 30;
- t is an integer of 2 to 200;
- and
- R7 is hydrogen or C1-4 alkyl;
- R2 is:
- 21
- where:
- x is an integer of 0 to 30;
- y is an integer of 2 to 200;
- R8 is hydrogen or C1-4 alkyl;
- R9 and R10 are independently C1-12 alkylene;
- R11 is hydrogen or C1-6 alkyl and R12 is C1-6 alkyl;
- or R11 and R12 together are C3-10 alkylene;
- and
- R4 is a diol containing at least one functional group independently selected from amide, imide, urea, and urethane groups;
- in which at least 0.1 mol % of the A units are R1, and at least 0.1 mol % of the A units are R4, the process comprising reacting a diketene acetal of formula II:
- 22
- where L is hydrogen or a C1-3 alkyl,
- with a diol of the formula HO—R1—OH and a diol of the formula HO—R4—OH, and optionally at least one diol of the formulae HO—R2—OH and HO—R3—OH.
31 more elements
A polyorthoester that is the product of a reaction between:
- (a) a diketene acetal of formula II:
- 23
- where L is hydrogen or a C1-3 alkyl, and
- (b) a polyol or mixture of polyols in which at least 0.1 mole percent of the total polyol content is a diol of the formula HO—R1—OH, where
- R1 is:
- 24
- where:
- p is an integer of 1 to 20;
- R5 is hydrogen or C1-4 alkyl;
- and
- R6 is:
- 25
- where:
- s is an integer of 0 to 30;
- t is an integer of 2 to 200;
- and
- R7 is hydrogen or C1-4 alkyl;
- R1 is hydrogen or C1-6 alkyl and R12 is C1-6 alkyl;
- or R11 and R11 together are C3-10 alkylene;
- and
- at least 0.1 mole percent of the total polyol content is a diol of the formula HO—R4—OH, where R4 is the residue of a diol containing at least one functional group independently selected from amide, imide, urea, and urethane groups.
18 more elements
Dependencies are inferred from the claim text.