Hydrophobic ceragenin compounds and devices incorporating same
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
A61K-031/56
A61F-013/00
C07J-051/00
C07J-041/00
A61L-027/52
A61L-027/54
A61L-031/14
A61L-031/16
A61L-027/34
A61L-029/08
A61L-029/14
A61L-029/16
A61L-031/10
C07C-211/00
A61L-027/18
출원번호
US-0602499
(2015-01-22)
등록번호
US-9546195
(2017-01-17)
발명자
/ 주소
Savage, Paul B.
출원인 / 주소
BRIGHAM YOUNG UNIVERSITY
대리인 / 주소
Workman Nydegger
인용정보
피인용 횟수 :
4인용 특허 :
34
초록▼
A hydrophobic cationic steroidal anti-microbial (ceragenin) compound forms an amphiphilic compound having a hydrophobic sterol face and a hydrophilic cationic face. The hydrophobic CSA also includes a hydrophobic substituent that gives the ceragenin compound a C Log P value of at least 6.0, 6.25, 6.
A hydrophobic cationic steroidal anti-microbial (ceragenin) compound forms an amphiphilic compound having a hydrophobic sterol face and a hydrophilic cationic face. The hydrophobic CSA also includes a hydrophobic substituent that gives the ceragenin compound a C Log P value of at least 6.0, 6.25, 6.5, 7.5, 8.5, or 10.
대표청구항▼
1. A hydrophobic cationic steroidal anti-microbial (CSA) compound comprising: a sterol structure comprising four fused carbon rings;at least one cationic substituent attached to each of at least three of the four fused carbon rings so as to form an amphiphilic compound having a hydrophobic sterol fa
1. A hydrophobic cationic steroidal anti-microbial (CSA) compound comprising: a sterol structure comprising four fused carbon rings;at least one cationic substituent attached to each of at least three of the four fused carbon rings so as to form an amphiphilic compound having a hydrophobic sterol face and a hydrophilic cationic face; andat least one hydrophobic substituent attached to at least one of the fused carbon rings;wherein the CSA compound has a structure as in Formula I: whereq=0 such that R18 is omitted, m and n are independently 0 or 1, and p=1;two or three of R3, R7, and R12 independently include a cationic group;R1-R4, R6, R7, R11, R12, R15, and R16 are independently selected from the group consisting of hydrogen, hydroxyl, substituted or unsubstituted (C1-C10) alkyl, (C1-C10) hydroxyalkyl, (C1-C10) alkyloxy-(C1-C10) alkyl, (C1-C10) alkylcarboxy-(C1-C10) alkyl, (C1-C10) alkylamino-(C1-C10)alkyl, (C1-C10) alkylamino-(C1-C10) alkylamino, (C1-C10) alkylamino-(C1-C10) alkylamino-(C1-C10) alkylamino, substituted or unsubstituted (C1-C10) aminoalkyl, substituted or unsubstituted aryl, substituted or unsubstituted arylamino-(C1-C10) alkyl, (C1-C10) haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, oxo, linking group attached to a second steroid, substituted or unsubstituted (C1-C10) aminoalkyloxy, substituted or unsubstituted (C1-C10) aminoalkyloxy-(C1-C10) alkyl, substituted or unsubstituted (C1-C10) aminoalkylcarboxy, substituted or unsubstituted (C1-C10) aminoalkylaminocarbonyl, substituted or unsubstituted (C1-C10) aminoalkylcarboxamido, H2N—HC(Q5)-C(O)—O—, H2N—HC(Q5)-C(O)—N(H)—, (C1-C10) azidoalkyloxy, (C1-C10) cyanoalkyloxy, P.G.-HN—HC(Q5)-C(O)—O—, (C1-C10) guanidinoalkyloxy, (C1-C10) quaternary ammonium alkylcarboxy, and (C1-C10) guanidinoalkyl carboxy, where Q5 is a side chain of an amino acid, and P.G. is an amino protecting group;R5, R8-R10, R13, and R14 are independently deleted when one or more of fused rings A, B, C, or D is unsaturated so as to complete the valency of the carbon atom at that site or, when fused rings A, B, C, and D are saturated, are independently selected from the group consisting of hydrogen, hydroxyl, substituted or unsubstituted (C1-C10) alkyl, (C1-C10) hydroxyalkyl, (C1-C10) alkyloxy-(C1-C10) alkyl, substituted or unsubstituted (C1-C10) aminoalkyl, substituted or unsubstituted aryl, (C1-C10) haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, oxo, linking group attached to a second steroid, substituted or unsubstituted (C1-C10) aminoalkyloxy, substituted or unsubstituted (C1-C10) aminoalkylcarboxy, substituted or unsubstituted (C1-C10) aminoalkylaminocarbonyl, H2N—HC(Q5)-C(O)—O—, H2N—HC(Q5)-C(O)—N(H)—, (C1-C10) azidoalkyloxy, (C1-C10) cyanoalkyloxy, P.G.-HN—HC(Q5)-C(O)—O—, (C1-C10) guanidinoalkyloxy, and (C1-C10) guanidinoalkylcarboxy, where Q5 is a side chain of an amino acid and PG. is an amino protecting group; andR17 is a hydrophobic substituent which includes a heteroatom and at least one hydrocarbon group comprising a carbon chain of at least 9 carbon atoms distal to the heteroatom, with the proviso that R16 does not form a fused ring with R17 and R17 does not include a total of 16 carbon atoms distal to the heteroatom. 2. The hydrophobic CSA compound as in claim 1, wherein the C Log P value is at least 6.5. 3. The hydrophobic CSA compound as in claim 1, wherein the C Log P value is at least 10. 4. The hydrophobic CSA compound as in claim 1, wherein the C Log P value is between 6.0 and 9.0. 5. The hydrophobic CSA compound as in claim 1, wherein the at least one hydrophobic substituent includes a trimethylsilane. 6. The hydrophobic CSA compound as in claim 1, wherein the at least one hydrocarbon group comprises a straight chain hydrocarbon. 7. The hydrophobic CSA compound as in claim 1, wherein the at least one hydrocarbon group distal to the heteroatom of R17 has 9-15 carbon atoms. 8. The hydrophobic CSA compound as in claim 1, wherein the at least one hydrocarbon group distal to the heteroatom of R17 comprises a carbon chain of at least 11 carbon atoms, with the proviso that the carbon chain does not contain 16 carbon atoms. 9. The hydrophobic CSA compound as in claim 1, wherein the at least one hydrocarbon group distal to the heteroatom of R17 comprises at least 17 carbon atoms. 10. The hydrophobic CSA compound as in claim 1, wherein the CSA compound of Formula I is selected from the group consisting of: 11. A device comprising a polymer structure and the hydrophobic CSA compound of claim 1 incorporated into the polymer structure with non-covalent interactions. 12. The device of claim 11, wherein the polymer structure comprises a polymer selected from the group consisting of polyvinyl alcohol, sodium polyacrylate, an acrylate polymer, polyethylene oxide, polyAMPS, polyvinylpyrrolidone, polyacrylamide, silicone, agarose, methylcellulose, hyaluronan, or a combination thereof. 13. The device of claim 11, wherein the device comprises a medical device selected from the group consisting of bone implant, bone pin, bone screw, tissue graft, endotracheal tube, coronary stent, peripheral stent, catheter, arterio-venous graft, by-pass graft, pacemaker or defibrillator lead, anastomotic clip, arterial closure device, patent foramen ovale closure device, and drug delivery balloon. 14. The device of claim 11, wherein the polymer structure includes a polymer coated on a substrate. 15. The device of claim 11, wherein the hydrophobic CSA compound elutes from the polymer structure in excess saline water at a rate of 0.1-100 μg/ml at 3 days. 16. A composition comprising at least one hydrophobic cationic steroidal anti-microbial (CSA) compound selected from the group consisting of: 17. The composition of claim 16, wherein the at least one hydrophobic CSA compound is selected from the group consisting of: 18. The composition of claim 16, wherein the at least one hydrophobic CSA compound comprises: 19. The composition of claim 16, wherein the at least one hydrophobic CSA compound comprises: 20. The composition of claim 16, wherein the at least one hydrophobic CSA compound comprises:
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