Unsymmetrical aromatic ether diacids and absorbable polymers therefrom
First Claim
Patent Images
1. A compound of formula I or a pharmaceutically acceptable salt thereof:
-
[R′
—
(Y)p—
O]q—
Ar—
[O—
(X)r—
R′
]s
Iwherein;
Ar is the aromatic portion of a diphenol;
X and Y are independently selected from;
—
CH2COO—
;
—
CH(CH3)COO—
;
—
CH2CH2OCH2COO—
;
—
CH2CH2CH2CH2CH2COO—
;
—
(CH2)yCOO—
where y is independently selected from 2-4 and 6-24; and
—
(CH2CH2O)zCH2COO—
where z is independently selected from 2-24;
provided that the groups represented by [R′
—
(Y)p—
O]q— and
—
[O—
(X)r—
R′
]s are different from one another;
R′
is selected from H, benzyl, and C1-6 alkyl;
p is selected from 1, 2, 3, 4, 5, and 6;
q is selected from 1, 2, and 3;
r is selected from 1, 2, 3, 4, 5, and 6; and
s is selected from 1, 2, and 3.
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Abstract
The present invention relates to compounds and compositions of formula I, which are unsymmetrical aromatic ether diacids, and polymers formed from the same.
[R′—(Y)p—O]q—Ar—[O—(X)r—R′]s I
The compounds are expected to be useful in a variety of medical and/or cosmetics applications. Polymers formed from the functionalized unsymmetrical aromatic ether diacids are expected to have controllable degradation profiles, enabling them to release an active component over a desired time range.
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Citations
34 Claims
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1. A compound of formula I or a pharmaceutically acceptable salt thereof:
-
[R′
—
(Y)p—
O]q—
Ar—
[O—
(X)r—
R′
]s
Iwherein; Ar is the aromatic portion of a diphenol; X and Y are independently selected from; —
CH2COO—
;—
CH(CH3)COO—
;—
CH2CH2OCH2COO—
;—
CH2CH2CH2CH2CH2COO—
;—
(CH2)yCOO—
where y is independently selected from 2-4 and 6-24; and—
(CH2CH2O)zCH2COO—
where z is independently selected from 2-24;provided that the groups represented by [R′
—
(Y)p—
O]q— and
—
[O—
(X)r—
R′
]s are different from one another;R′
is selected from H, benzyl, and C1-6 alkyl;p is selected from 1, 2, 3, 4, 5, and 6; q is selected from 1, 2, and 3; r is selected from 1, 2, 3, 4, 5, and 6; and s is selected from 1, 2, and 3. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34)
-
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3. A compound according to claim 2, wherein
y is independently selected from 2, 3, and 4; -
z is independently selected from 2, 3, and 4; p is selected from 1, 2, and 3; q is selected from 1, 2, and 3; r is selected from 1, 2, and 3; and s is selected from 1, 2, and 3.
-
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4. A compound according to claim 2, wherein
X and Y are independently selected from: -
—
CH2COO—
;—
CH(CH3)COO—
;—
CH2CH2OCH2COO—
; and—
CH2CH2CH2CH2CH2COO—
;p is selected from 1 and 2; q is selected from 1 and 2; r is selected from 1 and 2; and s is selected from 1 and 2.
-
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5. A compound according to claim 2, wherein Ar is an optionally substituted diphenolic residue selected from:
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6. A compound according to claim 5, wherein Ar is an optionally substituted diphenolic residue selected from:
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7. A compound according to claim 6, wherein Ar is an optionally substituted diphenolic residue of formula:
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8. A compound according to claim 6, wherein Ar is an optionally substituted diphenolic residue of formula:
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9. A compound according to claim 8, Ar is a diphenolic residue of formula:
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10. A compound according to claim 6, wherein Ar is an optionally substituted diphenolic residue of formula:
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11. A compound according to claim 6, wherein Ar is an optionally substituted diphenolic residue of formula:
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12. A compound according to claim 5, wherein:
each Ar group is independently substituted with 1, 2, or 3 R groups, wherein; R is independently selected from ═
O, O-glycosides, —
(CH2)0-2—
ORa, —
(CH2)0-2—
C6H5, —
(CH2)0-2—
CHO, Cl, F, Br, I, —
(CH2)0-2—
OC(O)—
Ra, —
(CH2)0-2—
CO2—
Ra, —
(C(CH3))0-2—
CO2—
Ra, —
(CH2)0-2—
CO2—
(CH2)1-2—
CO2—
Ra, —
(C(CH3))0-2—
CO2—
(CH2)1-2—
CO2—
Ra, —
(CH2)0-2—
CO—
Ra, —
O(CH2)0-2—
C6H5, —
O(CH2)1-2—
CO2—
Ra, —
O(C(CH3))1-2—
CO2—
Ra, —
O(CH2)1-2—
CO—
Ra, —
CO2(CH2)1-2—
CO2—
Ra, —
CO2(C(CH3))1-2—
CO2—
Ra, —
(CH2)0-2—
NO2, —
(CH2)0-2—
NRaRa, —
(CH2)0-2—
NRaCORa, —
(CH2)0-2—
NRaC(O)(CH2)1-2ORa, —
C6H5, —
C6H5ORa, and —
C6H5—
CH═
CHCO2Ra; and
,Ra is independently selected from H and C1-6 alkyl.
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13. A compound according to claim 2, wherein the compound is selected from:
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14. A compound according to claim 9, wherein the compound is selected from:
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15. A composition, comprising:
- at least two different compounds according to claim 1.
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16. A solvent for a drug, comprising:
- at least one compound according to claim 1.
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17. A nutritional composition, comprising at least one compound according to claim 1.
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18. The nutritional composition according to claim 17, wherein the diphenolic residue in the compound of formula I was derived from a compound that is a nutritional supplement or a food intermediary.
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19. A cosmetic composition, comprising at least one compound according to claim 1 and a cosmetic ingredient.
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20. A pharmaceutical composition, comprising at least one compound according to claim 1 and a pharmaceutically acceptable excipient.
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21. The composition according to claim 20, wherein the composition is suitable for administration via a route selected from oral, enteral, parenteral, topical, transdermal, ocular, vitreal, rectal, nasal, pulmonary, and vaginal.
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22. The composition according to claim 20, wherein the diphenolic residue in the compound of formula I was derived from a cancer preventing diphenol.
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23. The composition according to claim 22, further comprising:
- an anti-cancer agent.
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24. The composition according to claim 20, wherein the diphenolic residue in the compound of formula I was derived from a phenolic with antimicrobial properties.
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25. The composition according to claim 24, further comprising:
- an antimicrobial agent.
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26. The composition according to claim 20, wherein the diphenolic residue in the compound of formula I was derived from a phenolic with anti-inflammatory properties.
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27. The composition according to claim 26, further comprising:
- anti-inflammatory agent.
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28. The composition according to claim 20, wherein the diphenolic residue in the compound of formula I was derived from a phenolic with pain-reducing properties.
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29. The composition according to claim 28, further comprising:
- a pain reducing agent.
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30. The composition according to claim 20, wherein the diphenolic residue in the compound of formula I was derived from a phenolic with antioxidant properties.
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31. The composition according to claim 30, further comprising:
- an antioxidant agent.
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32. A compound according to claim 1, wherein Ar is a synthetic or naturally derived flavanoid diphenolic residue.
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33. A compound according to claim 32, wherein the flavanoid is selected from:
flavonoids, flavanones, flavones, flavanols, anthocyanidins, proanthocyanidins, procyanidolic oligomers (PCO), catechins, biflavans, polyphenols, rutin, rutinosides, hydroxyethylrutosides (HER), hesperidin, quercetin, quercetrin, polyphenols, catechin, epicatechin, epicatechin gallate, epigallocatechin gallate, leucoanthocyanins, anthocyanins, and isoflavones; and
glucosides or β
-glycosides thereof.
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34. A compound according to claim 33, wherein the isoflavone is selected from:
glycitein, daidzein, prunetin, biochanin A, orobol, santal, pratensein, formononetin, genistein, and glycitein; and
glucosides or β
-glycosides thereof.
Specification