Biodegradable polyesteramide copolymers for drug delivery
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IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C08G-069/44
C08L-077/12
A61K-031/165
C09D-177/12
A61K-047/34
A61K-009/70
출원번호
US-0252350
(2016-08-31)
등록번호
US-9873765
(2018-01-23)
우선권정보
EP-11171191 (2011-06-23)
발명자
/ 주소
Draaisma, Guy
Mihov, George
출원인 / 주소
DSM IP ASSETS, B.V.
대리인 / 주소
Bull, Kevin M.
인용정보
피인용 횟수 :
0인용 특허 :
84
초록▼
The present invention relates to a poly (ester amide) (PEA) having a chemical formula described by structural formula (IV), wherein m+p varies from 0.9-0.1 and q varies from 0.1 to 0.9m+p+q=1 whereby m or p could be 0n is about 5 to about 300; (pref. 50-200)R1 is independently selected from the gro
The present invention relates to a poly (ester amide) (PEA) having a chemical formula described by structural formula (IV), wherein m+p varies from 0.9-0.1 and q varies from 0.1 to 0.9m+p+q=1 whereby m or p could be 0n is about 5 to about 300; (pref. 50-200)R1 is independently selected from the group consisting of (C2-C20) alkylene, (C2-C20) alkenylene, —(R9—CO—O—R10—O—CO—R9)—, —CHR11—O—CO—R12—COOCR11— and combinations thereof;R3 and R4 in a single backbone unit m or p, respectively, are independently selected from the group consisting of hydrogen, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C6-C10)aryl, (C1-C6)alkyl, —(CH2)SH, —(CH2)2S(CH3), —CH2OH, —CH(OH)CH3, —(CH2)4NH3+, —(CH2)3NHC(═NH2+)NH2, —CH2COOH, —(CH2)COOH, —CH2—CO—NH2, —CH2CH2—CO—NH2, —CH2CH2COOH, CH3—CH2—CH(CH3)—, (CH3)2—CH—CH2—, H2N—(CH2)4—, Ph-CH2—, CH═C—CH2—, HO-p-Ph-CH2—, (CH3)2—CH—, Ph-NH—, NH—(CH2)3—C—, NH—CH═N—CH═C—CH2—.R5 is selected from the group consisting of (C2-C20)alkylene, (C2-C20)alkenylene, alkyloxy or oligoethyleneglycolR6 is selected from bicyclic-fragments of 1,4:3,6-dianhydrohexitols of structural formula (III); R7 is selected from the group consisting of (C6-C10)aryl (C1-C6)alkylR8 is —(CH2)4-;R9 or R10 are independently selected from C2-C12 alkylene or C2-C12 alkenylene.R11 or R12 are independently selected from H, methyl, C2-C12 alkylene or C2-C12 alkenylene whereby a is at least 0.05 and b is at least 0.05 and a+b=1.
대표청구항▼
1. An article or device comprising a bioactive agent and a biodegradable polyesteramide copolymer (PEA) according to the following formula: wherein m+p is from 0.9-0.1 and q is from 0.1 to 0.9;m+p+q=1 whereby one of m or p could be 0;n is about 5 to about 300;a is at least 0.05, b is at least 0.05,
1. An article or device comprising a bioactive agent and a biodegradable polyesteramide copolymer (PEA) according to the following formula: wherein m+p is from 0.9-0.1 and q is from 0.1 to 0.9;m+p+q=1 whereby one of m or p could be 0;n is about 5 to about 300;a is at least 0.05, b is at least 0.05, a+b=1, qa=q*a, and qb=q*b; wherein units of m (if present), units of p (if present), units of a, and units of b are all randomly distributed throughout the copolymer;R1 is independently selected from the group consisting of (C2-C20) alkylene, (C2-C20) alkenylene, —(R9—CO—O—R10—O—CO—R9)—, —CHR11—O—CO—R12—COOCR11— and combinations thereof;R3 and R4 in a single backbone unit m or p, respectively, are independently selected from the group consisting of hydrogen, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C6-C10)aryl, (C1-C6)alkyl, —(CH2)SH, —(CH2)2S(CH3), —CH2OH, —CH(OH)CH3, —(CH2)4NH3+, —(CH2)3NHC(═NH2+)NH2, —CH2COOH, —(CH2)COOH, —CH2—CO—NH2, —CH2CH2—CO—NH2, —CH2CH2COOH, CH3—CH2—CH(CH3)—, (CH3)2—CH—CH2—, H2N—(CH2)4—, Ph-CH2—, CH═C—CH2—, HO-p-Ph-CH2—, (CH3)2—CH—, Ph-NH—, NH—(CH2)3—C—, NH—CH═N—CH═C—CH2—;R5 is selected from the group consisting of (C2-C20)alkylene, (C2-C20)alkenylene, alkyloxy or oligoethyleneglycol;R6 is selected from bicyclic-fragments of 1,4:3,6-dianhydrohexitols of structural formula (III); R7 is selected from the group consisting of (C6-C10) aryl (C1-C6)alkyl;R8 is —(CH2)4—;R9 or R10 are independently selected from C2-C12 alkylene or C2-C12 alkenylene;R11 or R12 are independently selected from H, methyl, C2-C12 alkylene or C2-C12 alkenylene. 2. The article or device according to claim 1, wherein a is at least 0.15. 3. The article or device according to claim 1, wherein a is at least 0.5. 4. The article or device according to claim 1, wherein a is at least 0.8. 5. The article or device according to claim 1, wherein p=0, m=0.75, and a=0.5;wherein the m, qa, and qb units are randomly distributed;R1 is —(CH2)8—, R3 is (CH3)2—CH—CH2—, R5 is hexyl, and R7 is benzyl. 6. The article or device according to claim 1, wherein q=0.25, p=0.45, m=0.3, and a=0.5;wherein the m, p, qa, and qb units are randomly distributed;R1 is —(CH2)8—; R3 and R4 respectively, are (CH3)2—CH—CH2—; R5 is (C2-C20)alkylene; and R7 is benzyl. 7. The article or device according to claim 1, wherein q=0.25, p=0.45, m=0.3, and a=0.75;wherein the m, p, qa, and qb units are randomly distributed;R1 is —(CH2)8—; R4 is (CH3)2—CH—CH2—; and R7 is benzyl. 8. The article or device according to claim 1, wherein q=0.1, p=0.30, m=0.6, and a=0.5;wherein the m, p, qa, and qb units are randomly distributed;R1 —(CH2)4—; R3 and R4 respectively, are (CH3)2—CH—CH2—; R7 benzyl;and R5 is (C2-C20)alkylene. 9. The article or device according to claim 1, wherein R1 is independently selected from (C2-C20)alkylene. 10. The article or device according to claim 1, wherein R5 is (C2-C20)alkylene. 11. The article or device according to claim 10, wherein R5 is (C2-C20)alkylene. 12. The article or device according to claim 1, wherein the biodegradable polyesteramide copolymer has an Mn of about 15,000 to about 100,000 Daltons, as measured via GPC in THF with polystyrene as standard. 13. The article or device according to claim 1, wherein the biodegradable polyesteramide copolymer has an Mn of about 30,000 to about 80,000 Daltons, as measured via GPC in THF with polystyrene as standard. 14. The article or device according to claim 11, wherein the biodegradable polyesteramide copolymer has an Mn of about 15,000 to about 100,000 Daltons, as measured via GPC in THF with polystyrene as standard. 15. The article or device according to claim 11, wherein the biodegradable polyesteramide copolymer has an Mn of about 30,000 to about 80,000 Daltons, as measured via GPC in THF with polystyrene as standard. 16. The article or device according to claim 7, wherein R5 is (C2-C20)alkylene. 17. The article or device according to claim 16, wherein the biodegradable polyesteramide copolymer has an Mn of about 15,000 to about 100,000 Daltons, as measured via GPC in THF with polystyrene as standard. 18. The article or device according to claim 16, wherein the biodegradable polyesteramide copolymer has an Mn of about 30,000 to about 80,000 Daltons, as measured via GPC in THF with polystyrene as standard. 19. The article or device according to claim 1, wherein the article or the device is a film, a coating, a micelle, a catheter, a stent, a rod, a microparticle, a nanoparticle, or an implant. 20. The article or device according to claim 2, wherein the article or the device is a film, a coating, a micelle, a catheter, a stent, a rod, a microparticle, a nanoparticle, or an implant. 21. The article or device according to claim 3, wherein the article or the device is a film, a coating, a micelle, a catheter, a stent, a rod, a microparticle, a nanoparticle, or an implant. 22. The article or device according to claim 11, wherein the article or the device is a film, a coating, a micelle, a catheter, a stent, a rod, a microparticle, a nanoparticle, or an implant. 23. The article or device according to claim 14, wherein the article or the device is a film, a coating, a micelle, a catheter, a stent, a rod, a microparticle, a nanoparticle, or an implant. 24. The article or device according to claim 15, wherein the article or the device is a film, a coating, a micelle, a catheter, a stent, a rod, a microparticle, a nanoparticle, or an implant. 25. The article or device according to claim 16, wherein the article or the device is a film, a coating, a micelle, a catheter, a stent, a rod, a microparticle, a nanoparticle, or an implant. 26. The article or device according to claim 17, wherein the article or the device is a film, a coating, a micelle, a catheter, a stent, a rod, a microparticle, a nanoparticle, or an implant. 27. The article or device according to claim 18, wherein the article or the device is a film, a coating, a micelle, a catheter, a stent, a rod, a microparticle, a nanoparticle, or an implant. 28. The article or device according to claim 1, wherein the article or device is a drug delivery device for ophthalmology applications and the bioactive agent is a small molecule ophthalmic drug, or prodrug or metabolite thereof. 29. The article or device according to claim 2, wherein the article or device is a drug delivery device for ophthalmology applications and the bioactive agent is a small molecule ophthalmic drug, or prodrug or metabolite thereof. 30. The article or device according to claim 3, wherein the article or device is a drug delivery device for ophthalmology applications and the bioactive agent is a small molecule ophthalmic drug, or prodrug or metabolite thereof. 31. The article or device according to claim 11, wherein the article or device is a drug delivery device for ophthalmology applications and the bioactive agent is a small molecule ophthalmic drug, or prodrug or metabolite thereof. 32. The article or device according to claim 14, wherein the article or device is a drug delivery device for ophthalmology applications and the bioactive agent is a small molecule ophthalmic drug, or prodrug or metabolite thereof. 33. The article or device according to claim 15, wherein the article or device is a drug delivery device for ophthalmology applications and the bioactive agent is a small molecule ophthalmic drug, or prodrug or metabolite thereof. 34. The article or device according to claim 16, wherein the article or device is a drug delivery device for ophthalmology applications and the bioactive agent is a small molecule ophthalmic drug, or prodrug or metabolite thereof. 35. The article or device according to claim 17, wherein the article or device is a drug delivery device for ophthalmology applications and the bioactive agent is a small molecule ophthalmic drug, or prodrug or metabolite thereof. 36. The article or device according to claim 18, wherein the article or device is a drug delivery device for ophthalmology applications and the bioactive agent is a small molecule ophthalmic drug, or prodrug or metabolite thereof.
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