Methods and compositions for preventing or treating periodontal diseases
First Claim
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1. A method for preventing or treating a periodontal disease in a subject comprising administering to a subject a prophylactically or therapeutically effective amount of a compound of formula I:
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or a pharmaceutically acceptable salt or prodrug thereof, wherein;
eachindependently designates a double or triple bond;
R1, R2, and R3 are each independently OR, OX1, SR, SX2, N(R)2, NHX3, NRC(O)R, NRC(O)N(R)2, C(O)OR, C(O)N(R)2, SO2R, NRSO2R, C(O)R, or SO2N(R)2;
each R is independently selected from hydrogen or an optionally substituted group selected from C1-6 aliphatic, a 3-8 membered saturated, partially unsaturated, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or;
two R on the same nitrogen are taken together with the nitrogen to form a 5-8 membered heterocyclyl or heteroaryl ring having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur;
each X1 is independently a suitable hydroxyl protecting group;
each X2 is independently a suitable thiol protecting group;
each X3 is independently a suitable amino protecting group; and
R4 is NRC(O)R, NRC(O)N(R)2, C(O)OR, C(O)N(R)2, SO2R, NRSO2R, C(O)R, or SO2N(R)2.
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Abstract
Methods and compositions for preventing or treating periodontal diseases including gingivitis and periodontitis are provided. The invention also provides methods for preventing or treating secondary diseases within or beyond the oral cavity that are related to periodontal disease.
112 Citations
40 Claims
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1. A method for preventing or treating a periodontal disease in a subject comprising administering to a subject a prophylactically or therapeutically effective amount of a compound of formula I:
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or a pharmaceutically acceptable salt or prodrug thereof, wherein;
each independently designates a double or triple bond;
R1, R2, and R3 are each independently OR, OX1, SR, SX2, N(R)2, NHX3, NRC(O)R, NRC(O)N(R)2, C(O)OR, C(O)N(R)2, SO2R, NRSO2R, C(O)R, or SO2N(R)2;
each R is independently selected from hydrogen or an optionally substituted group selected from C1-6 aliphatic, a 3-8 membered saturated, partially unsaturated, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or;
two R on the same nitrogen are taken together with the nitrogen to form a 5-8 membered heterocyclyl or heteroaryl ring having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur;
each X1 is independently a suitable hydroxyl protecting group;
each X2 is independently a suitable thiol protecting group;
each X3 is independently a suitable amino protecting group; and
R4 is NRC(O)R, NRC(O)N(R)2, C(O)OR, C(O)N(R)2, SO2R, NRSO2R, C(O)R, or SO2N(R)2. - 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)
between the C10 and C11 carbons designates a triple bond. -
3. The method of claim 1 wherein the
between the C16 and C17 carbons designates a triple bond -
4. The method of claim 1 wherein the
between the C10 and C11 carbons and the C16 and C17 carbons designates a triple bond. -
5. The method of claim 1 wherein each
designates a double bond. -
6. The method of claim 1 wherein R1, R2, and R3 are each independently OR, OX1, SR, SX2, N(R)2, or NHX3.
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7. The method of claim 6 wherein R1, R2, and R3 are each independently OR or OX1.
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8. The method of claim 1 wherein R is independently selected from hydrogen or an optionally substituted C1-6 aliphatic group.
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9. The method of claim 1 wherein R is hydrogen.
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10. The method of claim 1 wherein R4 is C(O)OR, C(O)N(R)2, or SO2R.
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11. The method of claim 10 wherein R4 is C(O)OR.
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12. The method of claim 1 wherein the C18 carbon has an R configuration.
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13. The method of claim 1 wherein the C5 carbon has an S configuration, the C12 carbon has an R configuration and the C18 carbon has an R configuration.
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14. The method of claim 13 wherein each
designates a double bond; - R1, R2, and R3 are each OH; and
R4 is C(O)OH.
- R1, R2, and R3 are each OH; and
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15. The method of claim 1 wherein the compound of formula I is present within a pharmaceutical composition that includes a pharmaceutically acceptable carrier.
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16. The method of claim 15 wherein the pharmaceutical composition further includes an antimicrobial compound or a non-steroidal antiinflammatory compound.
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17. The method of claim 15 wherein the pharmaceutical composition further includes a COX-2 inhibitor.
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18. The method of claim 17 wherein the COX-2 inhibitor is selected from the group consisting of celecoxib, rofecoxib, and valdecoxib.
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19. The method of claim 15 wherein the pharmaceutical composition is administered topically to the subject'"'"'s oral cavity.
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20. The method of claim 19 wherein the pharmaceutical composition is in a form selected from the group consisting of solutions, suspensions, dispersions, ointments, creams, pastes, gels, powders, toothpastes, lozenges, salve, chewing gum, mouth sprays, pastilles, sachets, mouthwashes, aerosols, tablets, capsules, transdermal patches, toothpicks, foods, and dental floss.
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21. The method of claim 19 wherein the pharmaceutical composition is in a form selected from the group consisting of toothpastes, chewing gum, mouth sprays, mouthwashes, toothpicks, and dental floss.
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22. The method of claim 1 wherein the periodontal disease is gingivitis.
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23. The method of claim 1 wherein the periodontal disease is periodontitis.
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24. A pharmaceutical composition comprising a prophylactically or therapeutically effective amount of a compound of formula I:
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or a pharmaceutically acceptable salt or prodrug thereof;
and a pharmaceutically acceptable carrier, wherein;
the pharmaceutical composition is in the form of a toothpaste, chewing gum, mouth spray, mouthwash, toothpick, or dental floss;
each independently designates a double or triple bond;
R1, R2, and R3 are each independently OR, OX1, SR, SX2, N(R)2, NHX3, NRC(O)R, NRC(O)N(R)2, C(O)OR, C(O)N(R)2, SO2R, NRSO2R, C(O)R, or SO2N(R)2;
each R is independently selected from hydrogen or an optionally substituted group selected from C1-6 aliphatic, a 3-8 membered saturated, partially unsaturated, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or;
two R on the same nitrogen are taken together with the nitrogen to form a 5-8 membered heterocyclyl or heteroaryl ring having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur;
each X1 is independently a suitable hydroxyl protecting group;
each X2 is independently a suitable thiol protecting group;
each X3 is independently a suitable amino protecting group; and
R4 is NRC(O)R, NRC(O)N(R)2, C(O)OR, C(O)N(R)2, SO2R, NRSO2R, C(O)R, or SO2N(R)2. - View Dependent Claims (25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40)
between the C10 and C11 carbons designates a triple bond. -
26. The composition of claim 24 wherein the
between the C16 and C17 carbons designates a triple bond -
27. The composition of claim 24 wherein the
between the C10 and C11 carbons and the C16 and C17 carbons designates a triple bond. -
28. The composition of claim 24 wherein each
designates a double bond. -
29. The composition of claim 24 wherein R1, R2, and R3 are each independently OR, OX1, SR, SX2, N(R)2, or NHX3.
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30. The composition of claim 29 wherein R1, R2, and R3 are each independently OR or OX1.
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31. The composition of claim 24 wherein R is independently selected from hydrogen or an optionally substituted C1-6 aliphatic group.
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32. The composition of claim 24 wherein R is hydrogen.
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33. The composition of claim 24 wherein R4 is C(O)OR, C(O)N(R)2, or SO2R.
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34. The composition of claim 33 wherein R4 is C(O)OR.
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35. The composition of claim 24 wherein the C18 carbon has an R configuration.
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36. The composition of claim 24 wherein the C5 carbon has an S configuration, the C12 carbon has an R configuration and the C18 carbon has an R configuration.
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37. The composition of claim 24 wherein each
designates a double bond; - R1, R2, and R3 are each OH; and
R4 is C(O)OH.
- R1, R2, and R3 are each OH; and
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38. The composition of claim 24 further comprising an antimicrobial compound or a non-steroidal antiinflammatory compound.
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39. The composition of claim 24 further comprising a COX-2 inhibitor.
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40. The composition of claim 39 wherein the COX-2 inhibitor is selected from the group consisting of celecoxib, rofecoxib, and valdecoxib.
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Specification
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Current AssigneeBrigham and Women's Hospital Incorporated, Trustees of Boston University, University of Southern California
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Original AssigneeUniversity of Southern California
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InventorsSerhan, Charles N., Petasis, Nicos A., Van Dyke, Thomas E.
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Application NumberUS11/106,141Publication NumberTime in Patent OfficeDaysField of SearchUS Class Current424/49CPC Class CodesA61K 31/10 Sulfides; Sulfoxides; SulfonesA61K 31/16 Amides, e.g. hydroxamic acidsA61K 31/17 having the group >N—C(O)—N<...A61K 31/18 Sulfonamides compounds cont...A61K 31/185 Acids; Anhydrides, halides ...A61K 31/202 having three or more double...A61K 31/232 having three or more double...A61K 8/0208 Tissues; Wipes; PatchesA61K 8/0216 Solid or semisolid formsA61K 8/046 Aerosols; FoamsA61K 8/365 Hydroxycarboxylic acids; Ke...A61P 1/02 Stomatological preparations...A61Q 11/00 Preparations for care of th...
