WO1998020834B1 - Method for treatment of dermatological disorders - Google Patents
Method for treatment of dermatological disordersInfo
- Publication number
- WO1998020834B1 WO1998020834B1 PCT/IB1997/001428 IB9701428W WO9820834B1 WO 1998020834 B1 WO1998020834 B1 WO 1998020834B1 IB 9701428 W IB9701428 W IB 9701428W WO 9820834 B1 WO9820834 B1 WO 9820834B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acid
- compound
- dicarboxylic acid
- group
- alkyl
- Prior art date
Links
- 201000010099 disease Diseases 0.000 title claims abstract 15
- 150000001875 compounds Chemical class 0.000 claims abstract 32
- 125000000217 alkyl group Chemical group 0.000 claims abstract 20
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 18
- 125000003118 aryl group Chemical group 0.000 claims abstract 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 18
- 150000002148 esters Chemical class 0.000 claims abstract 10
- 125000003158 alcohol group Chemical group 0.000 claims abstract 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract 6
- 239000000203 mixture Substances 0.000 claims 15
- 239000002537 cosmetic Substances 0.000 claims 7
- WNLRTRBMVRJNCN-UHFFFAOYSA-N Adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 6
- BDJRBEYXGGNYIS-UHFFFAOYSA-N Azelaic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims 6
- WLJVNTCWHIRURA-UHFFFAOYSA-N Pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 claims 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N Sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims 6
- TYFQFVWCELRYAO-UHFFFAOYSA-N Suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 claims 6
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 claims 6
- 230000002500 effect on skin Effects 0.000 claims 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- NVKAWKQGWWIWPM-ABEVXSGRSA-N 17-β-hydroxy-5-α-Androstan-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 NVKAWKQGWWIWPM-ABEVXSGRSA-N 0.000 claims 3
- TVIDDXQYHWJXFK-UHFFFAOYSA-N Dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 claims 3
- 206010020880 Hypertrophy Diseases 0.000 claims 3
- 210000002374 Sebum Anatomy 0.000 claims 3
- 229960003604 Testosterone Drugs 0.000 claims 3
- 235000011037 adipic acid Nutrition 0.000 claims 3
- 239000001361 adipic acid Substances 0.000 claims 3
- 229960003473 androstanolone Drugs 0.000 claims 3
- 230000036760 body temperature Effects 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 201000009910 diseases by infectious agent Diseases 0.000 claims 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- 239000007788 liquid Substances 0.000 claims 3
- 230000000813 microbial Effects 0.000 claims 3
- 230000035515 penetration Effects 0.000 claims 3
- 230000028327 secretion Effects 0.000 claims 3
- 210000000434 stratum corneum Anatomy 0.000 claims 3
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 claims 3
- DXNCZXXFRKPEPY-UHFFFAOYSA-N tridecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCC(O)=O DXNCZXXFRKPEPY-UHFFFAOYSA-N 0.000 claims 3
- LWBHHRRTOZQPDM-UHFFFAOYSA-N undecanedioic acid Chemical compound OC(=O)CCCCCCCCCC(O)=O LWBHHRRTOZQPDM-UHFFFAOYSA-N 0.000 claims 3
- 206010000496 Acne Diseases 0.000 claims 2
- 206010068168 Androgenetic alopecia Diseases 0.000 claims 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N Catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims 2
- 208000001840 Dandruff Diseases 0.000 claims 2
- 206010020112 Hirsutism Diseases 0.000 claims 2
- 206010020863 Hypertrichosis Diseases 0.000 claims 2
- 206010020864 Hypertrichosis Diseases 0.000 claims 2
- 206010021197 Ichthyosis Diseases 0.000 claims 2
- 206010021198 Ichthyosis Diseases 0.000 claims 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims 2
- 241001303601 Rosacea Species 0.000 claims 2
- 208000008742 Seborrheic Dermatitis Diseases 0.000 claims 2
- 206010039793 Seborrhoeic dermatitis Diseases 0.000 claims 2
- 210000003491 Skin Anatomy 0.000 claims 2
- 208000006641 Skin Disease Diseases 0.000 claims 2
- 208000002474 Tinea Diseases 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 201000002996 androgenic alopecia Diseases 0.000 claims 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N benzohydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atoms Chemical group C* 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 230000001530 keratinolytic Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 201000004681 psoriasis Diseases 0.000 claims 2
- 125000002523 retinol group Chemical group 0.000 claims 2
- 201000004700 rosacea Diseases 0.000 claims 2
- IJFXRHURBJZNAO-UHFFFAOYSA-N 3-Hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 claims 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-Hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 claims 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims 1
- -1 amide derivative of salicylic acid Chemical class 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 150000001991 dicarboxylic acids Chemical class 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 150000003872 salicylic acid derivatives Chemical class 0.000 claims 1
- 230000002508 compound effect Effects 0.000 abstract 1
Abstract
A compound effect for the treatment of dermatological disorders comprises a mono- or diester of an α, φ-dicarboxylic acid, wherein the alcohol moiety of the said ester comprises a keratolytically active alcohol. The compound may have formula (I), where n is in the range of 6 and 12; m is in the range of 0 and 8; R' is selected from the group consisting of H, alkyl, aryl, alkenyl, benzyl, OH, NHR'', CONHR'' and COOR''; R'' is selected from the group consisting of H, alkyl, aryl, alkenyl, and benzyl; and Y is selected from the group consisting of H, alkyl, aryl, alkenyl, benzyl and X.
Claims
1. A compound, comprising: an α,ω-dicarboxylic acid covalcntly linked through an ester bond with at least one keratolytically active alcohol moiety, having the formula,
coox
where n is in the range of 6 and 4 to 12; m is in the range of 0 to 8; R' is selected from the group consisting of H, alkyl, aryl, alkenyl, benzyl, OR", NHR", CONHR" and COOR"; R" is selected from the group consisting of alkyl, aryl, alkenyl, and benzyl; and Y is selected from the group consisting of H, alkyl, aryl, alkenyl, benzyl and X.
2. The compound of claim 1, characterized in that the compound is a liquid at body temperature,
3. The compound of claim 1, wherein the α,ω-dicarboxylic acid moiety comprises about 6 to 14 carbon atoms.
4. The compound of claim 1, wherein the α,ω-dicarboxylic acid moiety comprises 8 to 10 carbon atoms.
5. The compound of claim 1, wherein the α,ω-dicarboxylic acid carbon chain backbone is unsaturated.
6. The compound of claim 5, wherein the backbone comprises about one to three double bonds.
7. The compound of claim 1, wherein ihe carbon chain of the α,ω- dicarboxylic acid moiety is linked to a hydrocarbon substituent.
8. The compound of claim 1, wherein the carbon chain of the α,ω- dicarboxylic acid moiety is substituted by alkyl, aryl, alkenyl or benzyl groups
9. The compound of claim 1, wherein said α,ω-dicarboxylic acid is selected from the group consisting of adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, 1,11-undecanedioic acid, 1,12-dodecanedioic acid, 1,13-tridecanedioic acid and 1,14- tetradecanedioic acid.
10. The compound of claim 1, wherein said α,ω-dicarboxylic acid comprises azelaic acid
11. The compound of claim 1, wherein said keratolytically active alcohol moiety comprises an ester, anhydride or amide derivative of salicylic acid or a derivative thereof.
12. A pharmaceutical or cosmetic composition, comprising: a therapeutically effective amount of a compound comprising a mono- or diester of an α,ω-dicarboxylic acid, wherein the ester comprises a keratolytically active alcohol moiety, having the formula, coox
13- tridecanedioic acid and 1,14-tetradecanedioic acid.
14. The pharmaceutical or cosmetic composition of claim 12, wherein the α,ω- dica boxylic acid comprises azelaic acid.
15. The composition of claim 12, wherein the compound is a liquid at body temperature.
16. The composition of claim 12, wherein the ",T-dicarboxylic acid carbon chain backbone is uπsaturated.
17. The composition of claim 16, wherein the backbone comprises about one to three double bonds.
18. The composition of claim 12, wherein the backbone of the ",T-dicarboxylic acid moiety is linked to a hydrocarbon substituent.
19. The composition of claim 12, wherein the backbone of the ",T-dicarboxylic acid moiety is substituted by alkyl, aryl, alkenyl or benzyl groups
20. The pharmaceutical or cosmetic composition of claim 12, wherein said keratolytic alcohol is selected from a group consisting of ortho-, meta- and para- hydroxybenzoic acid, ortho-, meta- and para-hydroxyalkylbenzoate, ortho-, meta-, and para-dihydroxybenzene, ortho-, meta-, and para-hydroxytoluene and derivatives thereof.
21. The pharmaceutical or cosmetic composition of claim 12, wherein said keratolytically active alcohol comprises an alkyl derivative of ortho-, meta- and para- hydroxyalkylbenzoate.
22. A pharmaceutical or cosmetic composition, comprising: a therapeutically effective amount of a compound comprising a mono- or diester of an α,ω-dicarboxylic acid, wherein the ester comprises a retinol moiety or derivatives thereof; and a pharmaceutically acceptable carrier.
23. The composition of claim 12 or 22, wherein said therapeutically effective amount of said compound comprises an amount effective to treat skin disorders.
24. The pharmaceutical or cosmetic composition of claim 12 or 22, wherein said therapeutically effective amount of said compound comprises an amount effective to treat dermatological disorders selected from the group consisting of hyperkeratinization, hypertrophy of the stratum corneum, excess sebum secretion, microbial infection, deπnatophycoses, or increased conversion of testosterone to dihydrotestosterone.
25. A method of treating dermatological disorders, comprising: administering topically, nasally, orally or parenterally to a subject having said dermatological disorder a therapeutically effective amount of a compound comprising a therapeutically effective amount of a compound comprising a mono-or diester of an α3ω-dicarboxy)ic acid, wherein at least one alcohol moiety of the said ester comprises a keratolytically active alcohol moiety, the compound having the formula to a subject having said dermatological disorder
coox
where n is in the range of 4 to 12; m is in the range of 0 to 8; R' is selected from the group consisting of H, alkyl, aryl, alkenyl, benzyl, OH, NHR", CONHR" and COOR"; R" is selected from the group consisting of alkyl, aryl, alkenyl, and benzyl; and Y is selected from the group consisting of H, alkyl, aryl, alkenyl, benzyl and X.
26. The method of claim 25, wherein said compound is applied topically to the affected area.
27. The method of claim 25 or 26, wherein the compound is a liquid at body temperature.
28. The method of claim 25 or 26, wherein said dermatological disorder is linked to hyperkeratinization, hypertrophy of the stratum corneum, excess sebum secretion, microbial infection, dermatophytoses, or increased conversion of testosterone to dihydrotestosterone.
29. The method of claim 25 or 26, wherein said dermatological disorder is selected from a group consisting of acne, seborrheic dermatitis, dandruff, psoriasis, ichthyosis, Rosacea, hirsutism, hypertrichosis, and androgenic alopecia,
30. The method of claim 25 or 26, wherein said dermatological disorder comprises dermatoses.
31. The method of claim 25 or 26, wherein said o,ω-dicarboxylic acid is selected from the group consisting of adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, 1,11-undecanedioic acid, 1,12-dodecanedioic acid, 1,13-tridecanedioic acid and 1,14-tetradecanedioic acid.
32. The method of claim 25 or 26, wherein the o,ω-dicarboxylic acid comprises azelaic acid.
33. The method of claim 25 or 26, wherein the α,ω-dicarboxylic acid carbon chain backbone is unsaturated. 29
34. The method of claim 25 or 26, wherein the backbone comprises about one to three double bonds,
35. The method of claim 25 or 26, wherein the carbon backbone of the α,ω-dicarboxylic acid moiety is substituted by a hydrocarbon substituent,
36. The method of claim 25 or 26, wherein the carbon backbone of the α,ω-dicarboxylic acid moiety is substituted by alkyl, aryl, alkenyl or benzyl groups
37. The method of claim 25 or 26, wherein said keratolytic alcohol moiety is selected from a group consisting of ortho-, meta-and para-hydroxyalkylbenzoates, ortho-, meta-, and para-dihydroxybenzene, ortho-, meta-, and para-hydroxytoluene and derivatives thereof.
38. The method of claim 25 or 26, wherein said keratolytically active alcohol moiety comprises an alkyl derivative of ortho-, meta-and para-hydroxyalkylbenzoate.
39. A method of treating dermatological disorders, comprising: administering topically, nasally, orally or parenterally to a subject having said dermatological disorder a therapeutically effective amount of a compound comprising a mono-or diester of an ,ω-dicarboxylic acid, wherein at least one of the said ester comprises a keratolytically active alcohol moiety, comprises a retinol moiety or derivatives thereof.
40. A method of increasing penetration of an α,ω-dicarboxylic acid across dermal layer, comprising: applying a mono or diester derivative of the α,ω-dicarboxylic acid to the dermal layer, said ester moiety comprises a keratolytically active alcohol.
41. A method of increasing penetration of a salicylic acid derivative across dermal layer, comprising: 30 applying a mono or disalicylate ester derivative of an α,ω-dicarboxylic acid to the dermal layer.
42. Compounds of claims 1 to 11, which are functional to release a plurality of dermatologically-active compounds when delivered to a target site of the skin,
43. Compositions of claims 12 to 24, which are functional to release a plurality of dermatologically-active compounds when delivered to a target site of the skin.
44. The compounds of any of claims 1 to 11, for use in treating dermatological disorders.
45. Use of a compound comprising a mono- or diester of an α,ω-dicarboxylic acid, wherein the ester moiety of the dicarboxylic acid comprises a keratolytically active alcohol, for the manufacture of a pharmaceutical composition in topically, orally or parenterally aα^ninistrable form, for treating dermatological disorders, said compound having the formula, coox
46. The use of claim 45, wherein the dermatological disorder is linked to hyperkeratinization, hypertrophy of the stratum corneum, excess sebum secretion, microbial infection, dermatophytoses, or increased conversion of testosterone to dihydrotestosterone. 31
47. The use of claim 45, wherein the dermatological disorder is selected from acne, seborrhoeic dermatitis, dandruff, psoriasis, ichthyosis, Rosacea, hirsutism, hypertrichosis and androgenic alopecia.
48. Use of a mono- or diester derivative of an α,ω-dicarboxylic acid wherein the ester moiety comprises a keratolytically active alcohol, for the manufacture of a composition for increasing penetration of the α,ω-dicarboxylic acid across a dermal layer.
49. The use according to any of claims 45 to 48, wherein the compound or derivative is a compound according to any of claims 1 to 11.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP52234098A JP2001509137A (en) | 1996-11-12 | 1997-11-12 | How to treat skin diseases |
| EP97911392A EP0946485A4 (en) | 1996-11-12 | 1997-11-12 | Method for treatment of dermatological disorders |
| CA002275867A CA2275867A1 (en) | 1996-11-12 | 1997-11-12 | Method for treatment of dermatological disorders |
| BR9713348-5A BR9713348A (en) | 1996-11-12 | 1997-11-12 | Method for treating dermatological disorders |
| AU48801/97A AU731832B2 (en) | 1996-11-12 | 1997-11-12 | Method for treatment of dermatological disorders |
| US09/286,236 US6180669B1 (en) | 1996-11-12 | 1999-04-05 | Method for treatment of dermatological disorders |
| MXPA/A/1999/004350A MXPA99004350A (en) | 1996-11-12 | 1999-05-11 | Method for treatment of dermatological disorders |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3051296P | 1996-11-12 | 1996-11-12 | |
| US60/030,512 | 1996-11-12 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US09/286,236 Continuation-In-Part US6180669B1 (en) | 1996-11-12 | 1999-04-05 | Method for treatment of dermatological disorders |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| WO1998020834A2 WO1998020834A2 (en) | 1998-05-22 |
| WO1998020834A3 WO1998020834A3 (en) | 1998-11-26 |
| WO1998020834B1 true WO1998020834B1 (en) | 1999-01-21 |
Family
ID=21854550
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IB1997/001428 WO1998020834A2 (en) | 1996-11-12 | 1997-11-12 | Method for treatment of dermatological disorders |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6180669B1 (en) |
| EP (1) | EP0946485A4 (en) |
| JP (1) | JP2001509137A (en) |
| KR (1) | KR20000053244A (en) |
| CN (1) | CN1237151A (en) |
| AU (1) | AU731832B2 (en) |
| BR (1) | BR9713348A (en) |
| CA (1) | CA2275867A1 (en) |
| NZ (1) | NZ335495A (en) |
| WO (1) | WO1998020834A2 (en) |
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| US1979559A (en) * | 1932-06-06 | 1934-11-06 | Monsanto Chemicals | Ester of hydroxybenzoic acid |
| US3462468A (en) * | 1964-10-22 | 1969-08-19 | Celanese Corp | Resorcinol esters of alpha,alpha-dimethyl aliphatic acids |
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-
1997
- 1997-11-12 AU AU48801/97A patent/AU731832B2/en not_active Ceased
- 1997-11-12 WO PCT/IB1997/001428 patent/WO1998020834A2/en not_active Application Discontinuation
- 1997-11-12 KR KR1019990704222A patent/KR20000053244A/en not_active Application Discontinuation
- 1997-11-12 BR BR9713348-5A patent/BR9713348A/en not_active IP Right Cessation
- 1997-11-12 JP JP52234098A patent/JP2001509137A/en active Pending
- 1997-11-12 CA CA002275867A patent/CA2275867A1/en not_active Abandoned
- 1997-11-12 CN CN97199643A patent/CN1237151A/en active Pending
- 1997-11-12 EP EP97911392A patent/EP0946485A4/en not_active Withdrawn
- 1997-11-12 NZ NZ335495A patent/NZ335495A/en unknown
-
1999
- 1999-04-05 US US09/286,236 patent/US6180669B1/en not_active Expired - Fee Related
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