Poly(orthoester) co- and homopolymers and poly(orthocarbonate) co- and homopolymers having carbonyloxy functionality

• US 4,070,347 A
• Filed: 08/16/1976
• Issued: 01/24/1978
• Est. Priority Date: 08/16/1976
• Status: Expired due to Term

• Current Assignee: ALZA Corporation (Johnson & Johnson)
• Original Assignee: ALZA Corporation (Johnson & Johnson)
• Inventors: Schmitt, Edward Emil
• Primary Examiner(s): Anderson, Harold D.
• Assistant Examiner(s): Nielsen, E. A.
• Application Number:
  US05/714,577
• Time in Patent Office: 526 Days
• Field of Search: 260/78.3 R, 260/77.5 D, 260/338, 260/340.7, 260/340.9, 260/345.9, 260/347.8
• US Class Current: 528/271
• CPC Class Codes: A61K 9/204 Polyesters, e.g. poly(lactide-co-glycolide)
• CPC Class Codes: C05G 3/44 for affecting solubility
• CPC Class Codes: C05G 5/37 layered or coated with a polymer
• CPC Class Codes: C08G 65/34 from hydroxy compounds or their metallic derivatives C08G65/26 takes precedence

Abstract

Poly(orthoester) co- and homopolymers and poly(orthocarbonate) co- and homopolymers comprising (1) a repeating dioxycarbon unit in the polymeric backbone having a plurality of organic groups pendant therefrom, and (2) a bridging moiety having at least one carbonyloxy group contained therein are disclosed. The polymers are represented by the formula: ##STR1## wherein R is a bridging moiety and is either R₁ or R₂ arranged in a random manner along the polymeric backbone to form a copolymer containing both R₁ and R₂ with R₁ an aliphatic, an alicyclic or an aromatic group and R₂ is a ##STR2## GROUP WITH R₁ as defined and R₃ an aliphatic, an alicyclic or aromatic group, or wherein R is a bridging moiety and is only R₂ to form a homopolymer with R₁, R₂ and R₃ as defined above, and a is 0 to 1, b is 2 to 6, and n and the sum of x and y are positive integers. The copolymers are useful for making articles of manufacture, including devices and coatings for delivering beneficial agents.

Claims

1. A polymer of the general formula:

##STR33## wherein R is a member selected from the group consisting of (1) R₁ and R₂ randomly arranged on the polymeric backbone to form a polymer containing both R₁ and R₂, and (2) R₂ only, with R₁ selected from the group consisting of alkylene of 1 to 10 carbons;

alkenylene of 2 to 10 carbons;

cycloalkylene of 3 to 7 carbons;

cycloalkylene of 3 to 7 carbons substituted with a member selected from the group consisting of an alkyl of 1 to 10 carbons, alkenyl of 2 to 10 carbons, alkoxy of 1 to 10 carbons and alkylene of 1 to 10 carbons;

cycloalkenylene of 5 to 7 carbons;

cycloalkenylene of 5 to 7 carbons substituted with a member selected from the group consisting of an alkyl of 1 to 10 carbons;

alkenyl of 2 to 10 carbons, alkoxy of 1 to 10 carbons and alkylene of 1 to 10 carbons;

arylene;

arylene of 6 to 20 carbons substituted with an alkyl of 1 to 10 carbons, alkenyl of 2 to 10 carbons, alkoxy of 1 to 10 carbons, and alkylene of 1 to 10 carbons; and

with R₂ a ##STR34## group with R₁ as defined and R₃ independently selected from the group consisting of alkylene of 1 to 10 carbons;

alkenylene of 2 to 10 carbons;

cycloalkylene of 3 to 7 carbons;

cycloalkylene of 3 to 7 carbons substituted with a member selected from the group consisting of an alkyl of 1 to 10 carbons, alkenyl of 2 to 10 carbons, alkoxy of 1 to 10 carbons and alkylene of 1 to 10 carbons;

cycloalkenylene of 5 to 7 carbons;

cycloalkenylene of 5 to 7 carbons substituted with a member selected from the group consisting of an alkyl of 1 to 10 carbons, alkenyl of 2 to 10 carbons, alkoxy of 1 to 10 carbons and alkylene of 1 to 10 carbons;

arylene;

arylene of 6 to 20 carbons substituted with an alkyl of 1 to 10 carbons, alkenyl of 2 to 10 carbons, alkoxy of 1 to 10 carbons and alkylene of 1 to 10 carbons; and

a is 0 to 1, b is 2 to 6, x and y are independently 0 to 100 with the proviso that at least one of x and y is at least one, and n is at least 10.

2. A copolymer according to claim 1 of the formula wherein m and n are 10 to 1000:

##STR35##

3. A copolymer according to claim 1 of the formula wherein m and n are 10 to 1000:

##STR36##

4. A copolymer according to claim 1 of the formula wherein m and n are 10 to 1000:

##STR37##

5. A copolymer according to claim 1 of the formula wherein m and n are 10 to 1000:

##STR38##

6. A copolymer according to claim 1 of the formula wherein m and n are 10 to 1000:

##STR39##

7. A copolymer according to claim 1 of the formula wherein m and n are 10 to 1000:

##STR40##

8. A copolymer according to claim 1 of the formula wherein m and n are 10 to 1000:

##STR41##

9. A copolymer according to claim 1 of the formula wherein m and n are 10 to 1000:

##STR42##

10. A copolymer according to claim 1 of the formula wherein m and n are 10 to 1000:

##STR43##

11. A homopolymer of the general formula:

##STR44## wherein R₁ is a member selected from the group consisting of alkylene of 1 to 10 carbons;

alkenylene of 2 to 10 carbons, cycloalkylene of 3 to 7 carbons;

cycloalkylene of 3 to 7 carbons substituted with a member selected from the group consisting of an alkyl of 1 to 10 carbons, alkenyl of 2 to 10 carbons, alkoxy of 1 to 10 carbons and alkylene of 1 to 10 carbons;

cycloalkenylene of 5 to 7 carbons;

cycloalkenylene of 5 to 7 carbons substituted with a member selected from the group consisting of an alkyl of 1 to 10 carbons, alkenyl of 2 to 10 carbons, alkoxy of 1 to 10 carbons and alkylene of 1 to 10 carbons;

arylene;

arylene of 6 to 20 carbons substituted with an alkyl of 1 to 10 carbons;

alkenyl of 2 to 10 carbons, alkoxy of 1 to 10 carbons and alkylene of 1 to 10 carbons; and

wherein R₃ is the same as R₁, a is 0 to 1, b is 2 to 6, n is 10 to 1000 and x and y are 0 to 100 with the proviso that one of x and y is always at least one.

12. A homopolymer according to claim 11 of the formula wherein x and y are at least one:

##STR45##

13. A homopolymer according to claim 11 of the formula wherein x and y are at least one:

##STR46##

14. A homopolymer according to claim 11 of the formula wherein x and y are at least one:

##STR47##

15. A homopolymer according to claim 11 of the formula wherein x and y are at least one:

##STR48##

16. A homopolymer according to claim 11 of the formula wherein x and y are at least one:

##STR49##

17. A homopolymer according to claim 11 of the formula wherein x and y are at least one:

##STR50##

18. A homopolymer according to claim 11 of the formula wherein x and y are at least one:

##STR51##

19. A homopolymer according to claim 11 of the formula wherein x and y are at least one:

##STR52##

20. A homopolymer according to claim 11 of the formula wherein x and y are at least one:

##STR53##

21. A homopolymer according to claim 11 of the formula wherein x and y are at least one:

##STR54##

22. A homopolymer according to claim 11 of the formula wherein x and y are at least one:

##STR55##

23. A homopolymer according to claim 11 of the formula wherein x and y are at least one:

##STR56##

24. A homopolymer according to claim 11 of the formula wherein x and y are least one:

##STR57##

25. A homopolymer accordng to claim 11 of the formula wherein x and y are at least one:

##STR58##

26. A homopolymer according to claim 11 of the formula wherein x and y are at least one:

##STR59##

27. A homopolymer according to claim 11 of the formula wherein the sum of x and y are at least one:

##STR60##

28. A homopolymer according to claim 11 of the formula wherein x and y are at least one:

##STR61##

29. A homopolymer according to claim 11 of the formula wherein x and y are at least one:

##STR62##

30. A homopolymer according to claim 11 of the formula wherein x and y are at least one:

##STR63##

31. A homopolymer according to claim 11 of the formula wherein x and y are at least one:

##STR64##

32. A homopolymer according to claim 11 of the formula wherein x and y are at least one:

##STR65##