Phosphorus-containing compounds with polymeric chains, and methods of making and using the same
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C08G-079/02
C08G-079/04
C08G-079/00
출원번호
US-0692233
(2010-01-22)
등록번호
US-8258255
(2012-09-04)
발명자
/ 주소
Branham, Keith
Chaubal, Mahesh V.
English, James P.
Hall, Donna
Zhao, Zhong
출원인 / 주소
Eisai Inc.
대리인 / 주소
Myers Bigel Sibley & Sajovec, P.A.
인용정보
피인용 횟수 :
0인용 특허 :
36
초록▼
The present invention relates to novel phosphorus-containing compounds with polymeric chains, and methods of making and using the same. In part, subject compositions containing phosphorus-containing compounds with polymeric chains and a therapeutic agent, and methods of making and using the same, ar
The present invention relates to novel phosphorus-containing compounds with polymeric chains, and methods of making and using the same. In part, subject compositions containing phosphorus-containing compounds with polymeric chains and a therapeutic agent, and methods of making and using the same, are described. Certain of the subject compositions exhibit reverse thermal gelation.
대표청구항▼
1. A composition, comprising: a phosphorus-containing compound represented by the following formula: wherein, independently for each occurrence:Q represents —O or —N(R3);r represents 0 or 1, and s represents 3 or 2, such that r+s=3;R1 is represented by: wherein* represents the central phosphorus ato
1. A composition, comprising: a phosphorus-containing compound represented by the following formula: wherein, independently for each occurrence:Q represents —O or —N(R3);r represents 0 or 1, and s represents 3 or 2, such that r+s=3;R1 is represented by: wherein* represents the central phosphorus atom of Formula I;R2 represents a polymeric chain that differs from R1 and does not interfere with the biocompatability of the compound;R3 represents —H, alkyl, aryl, cycloalkyl, cycloalkenyl, heterocycle, or polycycle;R7 represents —O-alkyl, —O-cycloalkyl, —O-aryl, —O-heterocyclyl, —S-alkyl, —S-cycloalkyl, —S-aryl, —S-heterocyclyl, or —N(R4)R5;R4 and R5, each independently, represent a hydrogen, an alkyl, an alkenyl, —(CH2)m-R6, or R4 and R5, taken together with the N atom to which they are attached complete a heterocycle having from 4 to about 8 atoms in the ring structure;m represents an integer from 0-10;R6 represents —H, alkyl, cycloakyl, —O-alkyl, —O-cycloalkyl, cycloalkenyl, —O-cycloalkenyl, aryl, —O-aryl, heterocycle, —O-heterocycle, polycycle or —O-polycycle;Q1, Q2 . . . Qs, each independently, represent —O or —N(R3);X1, X2 . . . Xs, each independently, represent —O —or —N(R3)—;ts is a constitutional unit of the polymeric chain;the s of ts is an integer and at least 1;n1, n2 . . . n3 is greater than 0 to about 1000;x is an integer from 1 to about 1000; andM1, M2 . . . Ms each independently represent an aliphatic or aryl group. 2. A composition, comprising: a phosphorus-containing compound represented by the following formula: wherein, independently for each occurrence:Q represents —O or —N(R3);r represents 0 or 1, and s represents 3 or 2, such that r+s=3;R1 is represented by wherein* represents the central phosphorus atom of Formula I;R2 represents a polymeric chain that differs from R1 and does not interfere with the biocompatability of the compound;R3 represents —H, alkyl, aryl, cycloalkyl, cycloalkenyl, heterocycle, or polycycle;R7 represents —O-alkyl, —O-cycloalkyl, —O-aryl, —O-heterocyclyl, —S-alkyl, —S-cycloalkyl, —S-aryl, —S-heterocyclyl, or —N(R4)R5;R4 and R5, each independently, represent a hydrogen, an alkyl, an alkenyl, —(CH2)m-R6, or R4 and R5, taken together with the N atom to which they are attached complete a heterocycle having from 4 to about 8 atoms in the ring structure;m represents an integer from 0-10;R6 represents —H, alkyl, cycloakyl, —O-alkyl, —O-cycloalkyl, cycloalkenyl, —O-cycloalkenyl, aryl, —O-aryl, heterocycle, —O-heterocycle, polycycle or —O-polycycle;Q1 represents —O or —N(R3);M1 and M2 each independently represent an aliphatic or aryl group;X1 and X2 each independently, represent —O — or —N(R3);x is an integer equal to at least 1;n1 and n2 are equal to 1; andthe t1 and t2 units may be in any order for each occurrence of the unit x. 3. The composition of claim 1, wherein Q represents O. 4. The composition of claim 2, wherein Q represents O. 5. The composition of claim 2, wherein M1 and M2 are each independently selected from the group consisting of —CH(CH3)—; —CH(CH3)CO2CH(CH3)—; —(CH2)d—; and —(CH2)d—O—; wherein d is from 1 to about 12. 6. The composition of claim 1, wherein R7 is represented by —O-alkyl. 7. The composition of claim 4, wherein R7 is represented by —O-alkyl. 8. A composition, comprising: a phosphorus-containing compound represented by the following formula: wherein, independently for each occurrence:Q represents —O or —N(R3);r represents 0 or 1, and s represents 3 or 2, such that r+s=3;R1 is represented by: wherein* represents the central phosphorus atom of Formula I;R2 represents a polymeric chain that differs from R1 and does not interfere with the biocompatability of the compound;R3 represents —H, alkyl, aryl, cycloalkyl, cycloalkenyl, heterocycle, or polycycle;M1 and M2 are each independently selected from the group consisting of —CH(CH3)—; —CH(CH3)CO2CH(CH3)—; —(CH2)d—; and —(CH2)d—O—; wherein d is from 1 to about 12;R7 is represented by —O-alkyln1 and n2 are equal to 1;the t1 and t2 units may be in any order for each occurrence of the unit x; andx is an integer from 1 to about 20. 9. A composition, comprising: a phosphorus-containing compound represented by the following formula: wherein, independently for each occurrence:Q represents —O or —N(R3);r represents 0 or 1, and s represents 3 or 2, such that r+s=3;R1 is represented by wherein* represents the central phosphorus atom of Formula I;R2 represents a polymeric chain that differs from R1 and does not interfere with the biocompatability of the compound;R3 represents —H, alkyl, aryl, cycloalkyl, cycloalkenyl, heterocycle, or polycycle;R7 represents —O—(CH2)mCH3 or —O—(CH2CH2O)mCH3, wherein m is at least 1;n1 and n2 are on average for each polymeric chain in the compound equal to about 2 and 2 or about 5.5 and 1.8, respectively;the t1 and t2 units may be in any order for each occurrence of the unit x; andx is equal to 1. 10. A composition, comprising: a phosphorus-containing represented by the following formula: wherein, independently for each occurrence:Q represents —O or —N(R3);r represents 0 or 1, and s represents 3 or 2, such that r+s=3;R1 is wherein* represents the central phosphorus atom of Formula I;R2 represents a polymeric chain that differs from R1 and does not interfere with the biocompatability of the compound;R3 represents —H, alkyl, aryl, cycloalkyl, cycloalkenyl, heterocycle, or polycycle;R7 represents —O—(CH2)mCH3, wherein m is at least 1;n1 and n2 are on average for each unit x are equal to about 2.4 and 1.6, respectively;the t1 and t2 units may be in any order for each occurrence of the unit x; andx is at least 1. 11. A composition, comprising: a phosphorus-containing compound represented by the following formula: wherein, independently for each occurrence:Q represents —O or —N(R3);r represents 0 or 1, and s represents 3 or 2, such that r+s=3;R1 is represented by: wherein* represents the central phosphorus atom of Formula I;M1 is selected from the group consisting of —CH(CH3)—; —CH(CH3)CO2CH(CH3)—; —(CH2)d—; and —(CH2)d—O—; wherein d is from 1 to about 12;Q1 represents —O or N(R3);R2 represents a polymeric chain that differs from R1 and does not interfere with the biocompatability of the compound;R3 represents —H, alkyl, aryl, cycloalkyl, cycloalkenyl, heterocycle, or polycycle;R7 represents —O—(CH2)mCH3, wherein m is at least 1; andx is an integer equal to at least 2. 12. A composition, comprising: a phosphorus-containing compound represented by the following formula: wherein, independently for each occurrence:Q represents —O or —N(R3);r represents 0 or 1, and s represents 3 or 2, such that r+s=3;R1 is represented by: wherein* represents the central phosphorus atom of Formula I;R2 represents a polymeric chain that differs from R1 and does not interfere with the biocompatability of the compound;R3 represents —H, alkyl, aryl, cycloalkyl, cycloalkenyl, heterocycle, or polycycle; andR7 represents —O—(CH2)mCH3, wherein m is at least 1, and x is at least 2. 13. The composition of claim 1, wherein said phosphorus-containing compound is amphiphilic. 14. The composition of claim 1, wherein said phosphorus-containing compound exhibits reverse thermal gelation. 15. The composition of claim 14, wherein said phosphorus-containing compound has a gelation temperature of below about 37° C. 16. The composition of claim 1, wherein R2 is selected from the group consisting of poly(ethylene glycol), poly(vinyl alcohols), poly(ethylene glycol)-co(polypropylene glycol), poly(ethylene glycol)-block-(polypropylene glycol), polyamides, polycarbonates, polyalkylenes, polyacrylamides, polyanhydrides, poly(phosphoesters), polyalkylene glycols, polyalkylene oxides, polyalkylene terephthalates, polyvinyl ethers, polyvinyl esters, polyvinyl halides, polyvinylpyrrolidone, polyglycolides, polysiloxanes, polyphosphates, polyurethanes, alkyl celluloses, hydroxyalkyl celluloses, cellulose ethers, cellulose esters, and nitrocelluloses.
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