Functionalized phenolic compounds and polymers therefrom

• US 8,802,892 B2
• Filed: 10/17/2012
• Issued: 08/12/2014
• Est. Priority Date: 10/21/2005
• Status: Active Grant

• Current Assignee: Bezwada Biomedical, LLC
• Original Assignee: Bezwada Biomedical, LLC
• Inventors: Bezwada, Rao S
• Primary Examiner(s): Schnizer, Richard
• Assistant Examiner(s): Pipic, Alma
• Application Number:
  US13/654,068
• Publication Number:
  US 20130281652A1
• Time in Patent Office: 664 Days
• Field of Search: 560/8, 560/67, 560/70, 560/75, 560/85, 562/405, 562/490, 562/493
• US Class Current: 562/405
• CPC Class Codes: A23L 29/288 Synthetic resins, e.g. polyvinylpyrrolidone
• CPC Class Codes: A23L 33/10 using additives addition of substantially indigestible substances A23L33/21
• CPC Class Codes: A23L 33/105 Plant extracts, their artificial duplicates or their derivatives
• CPC Class Codes: A61K 2800/522 Antioxidants; Radical scavengers
• CPC Class Codes: A61K 8/37 Esters of carboxylic acids
• CPC Class Codes: A61L 27/18 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: A61L 31/04 Macromolecular materials
• CPC Class Codes: A61L 31/10 Macromolecular materials
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: A61P 31/00 Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: A61Q 19/08 Anti-ageing preparations
• CPC Class Codes: C07C 205/37 the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
• CPC Class Codes: C07C 217/84 the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
• CPC Class Codes: C07C 233/18 having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
• CPC Class Codes: C07C 233/25 having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
• CPC Class Codes: C07C 65/21 containing ether groups, groups, groups, or groups
• CPC Class Codes: C07C 65/24 polycyclic
• CPC Class Codes: C07C 69/712 the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07C 69/732 : of unsaturated hydroxy carboxylic acids
• CPC Class Codes: C07C 69/734 : Ethers
• CPC Class Codes: C07C 69/92 : with etherified hydroxyl groups
• CPC Class Codes: C07D 311/12 : substituted in position 3 and unsubstituted in position 7
• CPC Class Codes: C07D 311/16 : substituted in position 7
• CPC Class Codes: C07D 311/36 : not hydrogenated in the hetero ring, e.g. isoflavones
• CPC Class Codes: C07D 493/04 : Ortho-condensed systems
• CPC Class Codes: C08G 63/66 : Polyesters containing oxygen in the form of ether groups C08G63/42, C08G63/58 take precedence
• CPC Class Codes: C08G 69/40 : Polyamides containing oxygen in the form of ether groups C08G69/12, C08G69/32 take precedence
• CPC Class Codes: C08G 69/44 : Polyester-amides
• CPC Class Codes: C08L 67/04 : Polyesters derived from hydroxycarboxylic acids, e.g. lactones C08L67/06 takes precedence

Abstract

The present invention relates to compounds of formula I, which are functionalized phenolic compounds, and polymers formed from the same.
Ar—[O—(X)_p—R′]_q  I
Polymers formed from the functionalized phenolics are expected to have controllable degradation profiles, enabling them to release an active component over a desired time range. The polymers are also expected to be useful in a variety of medical applications.

Claims

1. A compound of formula (I) or a pharmaceutically acceptable salt thereof:

Ar—

[O—

(X)_p—

R′

]_q 

 

(I)

wherein;

Ar is the remainder of a phenolic residue and is selected from;

resorcinol, catechol, dihydroxy-naphthyl, tri-hydroxy-naphthyl, tetra-hydroxy-naphthyl, unsubstituted hydroquinone, tri-hydroxy-phenyl, di-hydroxy-benzoic acids, and isoflavones;

X is independently at each occurrence selected

from;

—

CH₂COO—

;

—

CH(CH₃)COO—

;

—

CH₂CH₂OCH₂COO—

;

—

CH₂CH₂CH₂CH₂CH₂COO—

;

—

(CH₂)_yCOO—

; and

, —

(CH₂CH₂O)_zCH₂COO—

;

y is independently selected from 2, 3, 4 and 6-24;

z is independently selected from 2-24;

R′

is selected from H, benzyl, and C_1-6 alkyl;

p is independently selected from 2, 3, and 4; and

,

q is selected from 2, 3, 4, 5, 6, 7, 8, 9, and 10.

2. The compound according to claim 1, wherein

X is selected from:

—

CH₂COO—

;

—

CH(CH₃)COO—

;

—

CH₂CH₂OCH₂COO—

; and

,

—

CH₂CH₂CH₂CH₂CH₂COO—

; and

,

q is 2.

3. The compound according to claim 1, wherein

X is independently at each occurrence selected

from:

—

CH₂COO—

;

—

CH(CH₃)COO—

;

—

CH₂CH₂OCH₂COO—

;

—

CH₂CH₂CH₂CH₂CH₂CO O—

;

—

(CH₂)_yCOO—

; and

, —

(CH₂CH₂O)_zCH₂COO—

;

y is independently selected from 2, 3, and 4;

z is independently selected from 2, 3, and 4;

p is independently selected from 2 and 3; and

,

q is selected from 2 and 3.

4. The compound according to claim 1, wherein:

the phenolic residue is a di-hydroxy-benzoic acid.

5. A compound according to claim 1, wherein:

the phenolic residue is an isoflavone.

6. The compound of claim 1, wherein the phenolic residue is selected from:

resorcinol, catechol, unsubstituted hydroquinone, tri-hydroxy-phenyl, and dihydroxy-benzoic acid.

7. The compound of claim 1, wherein the compound is:

8. The compound of claim 1, wherein the compound is:

9. The compound of claim 1, wherein the compound is:

10. The compound of claim 1, wherein the phenolic residue and is an isoflavone that is selected from:

glycitein, daidzein, prunetin, biochanin A, orobol, santal, pratensein, and genistein.

11. The compound of claim 1, wherein the compound is

12. The compound of claim 1, wherein the phenolic residue is selected from:

resorcinol, catechol, unsubstituted hydroquinone, and tri-hydroxy-phenyl.

13. The compound of claim 1, wherein the phenolic residue is selected from:

dihydroxy-naphthyl, tri-hydroxy-naphthyl, and tetra-hydroxy-napthyl.