CA2482320A1 - Methods for modulating phototoxicity - Google Patents
Methods for modulating phototoxicity Download PDFInfo
- Publication number
- CA2482320A1 CA2482320A1 CA002482320A CA2482320A CA2482320A1 CA 2482320 A1 CA2482320 A1 CA 2482320A1 CA 002482320 A CA002482320 A CA 002482320A CA 2482320 A CA2482320 A CA 2482320A CA 2482320 A1 CA2482320 A1 CA 2482320A1
- Authority
- CA
- Canada
- Prior art keywords
- modulator
- alkyl
- carbon atoms
- compound
- proline
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 206010034972 Photosensitivity reaction Diseases 0.000 title 1
- 208000007578 phototoxic dermatitis Diseases 0.000 title 1
- 231100000018 phototoxicity Toxicity 0.000 title 1
- 230000008832 photodamage Effects 0.000 claims abstract 6
- 102000008186 Collagen Human genes 0.000 claims abstract 2
- 108010035532 Collagen Proteins 0.000 claims abstract 2
- 229920001436 collagen Polymers 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 5
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 claims 4
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 3
- 229960002429 proline Drugs 0.000 claims 3
- 229960002591 hydroxyproline Drugs 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- -1 4-hydroxy-L-proline alkyl ester compound Chemical class 0.000 claims 1
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 claims 1
- LCYXYLLJXMAEMT-SAXRGWBVSA-N Pyridinoline Chemical compound OC(=O)[C@@H](N)CCC1=C[N+](C[C@H](O)CC[C@H](N)C([O-])=O)=CC(O)=C1C[C@H](N)C(O)=O LCYXYLLJXMAEMT-SAXRGWBVSA-N 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 239000006071 cream Substances 0.000 claims 1
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000006210 lotion Substances 0.000 claims 1
- ZORHSASAYVIBLY-AKGZTFGVSA-N methyl (2s)-4-hydroxypyrrolidine-2-carboxylate Chemical compound COC(=O)[C@@H]1CC(O)CN1 ZORHSASAYVIBLY-AKGZTFGVSA-N 0.000 claims 1
- 125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- RADKZDMFGJYCBB-UHFFFAOYSA-N pyridoxal hydrochloride Natural products CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 claims 1
- 239000002453 shampoo Substances 0.000 claims 1
- 239000007921 spray Substances 0.000 claims 1
- 239000011726 vitamin B6 Substances 0.000 claims 1
- 235000019158 vitamin B6 Nutrition 0.000 claims 1
- 229940011671 vitamin b6 Drugs 0.000 claims 1
- 230000006378 damage Effects 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/004—Aftersun preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/401—Proline; Derivatives thereof, e.g. captopril
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/16—Emollients or protectives, e.g. against radiation
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/57—Compounds covalently linked to a(n inert) carrier molecule, e.g. conjugates, pro-fragrances
Abstract
The invention relates to methods for modulating photodamage via the use of collagen derived molecules which either enhance or inhibit damage caused by ultraviolet light.
Claims (20)
- Claim 1. A method for modulating photodamage in a subject in need thereof, comprising applying to skin of said subject an amount of a photodamage modulator sufficient to modulate photodamage caused by ultraviolet light.
- Claim 2. The method of claim 1, wherein said modulator enhances photodamage.
- Claim 3. The method of claim 2, wherein said modulator is collagen derived.
- Claim 4. The method of claim 2, wherein said modulator has a structure which consists of a 3-hydroxypyridine pharmacophore.
- Claim 5. The method of claim 4, wherein said modulator is an N-alkyl-3-hydroxypyridine or salt thereof.
- Claim 6. The method of claim 5, wherein said N-alkyl-3-hydroxypyridine or salt thereof comprises an alkyl moiety of 2-20 carbon atoms.
- Claim 7. The method of claim 6, wherein said alkyl moiety is an ethyl group.
- Claim 8. The method of claim 2, wherein said modulator is connected to a carrier molecule.
- Claim 9. The method of claim 2, wherein said modulator is vitamin B6, pyridinoline, or 3-hydroxypyridine.
- Claim 10. The method of claim 1, wherein said modulator inhibits photodamage.
- Claim 11. The method of claim 10, wherein said modulator is proline, 4-hydroxyproline or an alkyl ester thereof.
- Claim 12. The method of claim 11, wherein said proline alkyl ester comprises an alkyl moiety of 1-24 carbon atoms.
- Claim 13. The method of claim 12, wherein said proline alkyl ester is L-proline-OCH3 or 4-OH-L-Pro-OCH3.
- Claim 14. The method of claim 1, comprising applying said modulator m the form of a cream, lotion, shampoo, spray or patch.
- Claim 15. A 4-hydroxy-L-proline alkyl ester compound having an alkyl chain which contains from 1 to 24 carbon atoms.
- Claim 16. The compound of claim 15, which has a log P from about -1.00 to about +8.00.
- Claim 17. The compound of claim 15, wherein said alkyl chain contains 1-10 carbon atoms.
- Claim 18. The compound of claim 15, wherein said alkyl chain contains from 16 to 22 carbon atoms.
- Claim 19. The compound of claim 15, wherein said alkyl chain contains from 11-carbon atoms.
- Claim 20. The compound of claim 15, designated 4-hydroxy-L-proline methyl ester.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2668311A CA2668311C (en) | 2002-04-19 | 2003-04-17 | Enhancing photodamage caused by ultraviolet light using a 3-hydroxypyridine analog |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37403302P | 2002-04-19 | 2002-04-19 | |
| US60/374,033 | 2002-04-19 | ||
| PCT/US2003/011842 WO2003088909A2 (en) | 2002-04-19 | 2003-04-17 | Methods for modulating phototoxicity |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2668311A Division CA2668311C (en) | 2002-04-19 | 2003-04-17 | Enhancing photodamage caused by ultraviolet light using a 3-hydroxypyridine analog |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2482320A1 true CA2482320A1 (en) | 2003-10-30 |
| CA2482320C CA2482320C (en) | 2010-02-09 |
Family
ID=29251125
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2482320A Expired - Fee Related CA2482320C (en) | 2002-04-19 | 2003-04-17 | Methods for modulating phototoxicity |
| CA2668311A Expired - Fee Related CA2668311C (en) | 2002-04-19 | 2003-04-17 | Enhancing photodamage caused by ultraviolet light using a 3-hydroxypyridine analog |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2668311A Expired - Fee Related CA2668311C (en) | 2002-04-19 | 2003-04-17 | Enhancing photodamage caused by ultraviolet light using a 3-hydroxypyridine analog |
Country Status (17)
| Country | Link |
|---|---|
| US (3) | US6992071B2 (en) |
| EP (1) | EP1496891B1 (en) |
| JP (2) | JP4527405B2 (en) |
| CN (1) | CN1298321C (en) |
| AT (1) | ATE516802T1 (en) |
| AU (1) | AU2003234119B2 (en) |
| CA (2) | CA2482320C (en) |
| CY (1) | CY1112194T1 (en) |
| DK (1) | DK1496891T3 (en) |
| ES (1) | ES2367258T3 (en) |
| HK (1) | HK1077761B (en) |
| IL (2) | IL164560A0 (en) |
| MX (1) | MXPA04010228A (en) |
| NZ (1) | NZ535982A (en) |
| PT (1) | PT1496891E (en) |
| RU (1) | RU2301800C2 (en) |
| WO (1) | WO2003088909A2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1496891E (en) * | 2002-04-19 | 2011-09-02 | Univ Arizona State | Methods for modulating phototoxicity |
| EP2265105A1 (en) * | 2008-03-10 | 2010-12-29 | Basf Se | Encapsulated phase change materials in seed coatings |
| CN102365086A (en) * | 2009-03-30 | 2012-02-29 | 株式会社资生堂 | Composition for alleviating ultraviolet radiation-induced damage |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4310461A (en) * | 1980-06-23 | 1982-01-12 | E. R. Squibb & Sons, Inc. | Imido, amido and amino derivatives of mercaptoacyl prolines and pipecolic acids |
| US4902684A (en) * | 1988-06-20 | 1990-02-20 | E. R. Squibb & Sons, Inc. | Benzazepine and benzothiazepine derivatives |
| US6309440B1 (en) * | 1998-08-25 | 2001-10-30 | Thomas T. Yamashita | Method and composition for promoting and controlling growth of plants |
| US5208249A (en) * | 1992-08-20 | 1993-05-04 | Clintec Nutrition Co. | Method for stimulating intracellular synthesis of glutathione using esters of L-2-oxothiazolidine-4-carboxylate |
| JPH0797322A (en) * | 1993-09-29 | 1995-04-11 | Shiseido Co Ltd | Singlet oxygen elimination agent |
| US6013250A (en) * | 1995-06-28 | 2000-01-11 | L'oreal S. A. | Composition for treating hair against chemical and photo damage |
| US5681554A (en) * | 1995-06-28 | 1997-10-28 | Cosmair, Inc. | Composition for treating hair and method for using the same |
| JP2961074B2 (en) * | 1995-09-06 | 1999-10-12 | 明治製菓株式会社 | Neovascular occlusive agents for photochemotherapy |
| JPH09249567A (en) * | 1996-01-12 | 1997-09-22 | Otsuka Pharmaceut Co Ltd | Medicinal composition |
| DE69726144T9 (en) * | 1996-05-07 | 2004-09-09 | Bernstein, Eric F. | TOPICAL USE OF TEMPOL TO PREVENT LIGHT AGING |
| US20010056085A1 (en) * | 1996-07-09 | 2001-12-27 | Avner Ramu | Methods of using vesicant drug formulations |
| US6274564B1 (en) * | 1996-09-18 | 2001-08-14 | William J. Sarill | Compositions of cobalamin and related corrinoids, and uses thereof |
| AU732214C (en) * | 1997-03-31 | 2001-10-25 | Wakamoto Pharmaceutical Co., Ltd. | Biphenyl derivatives and drug composition |
| US6103487A (en) * | 1997-08-27 | 2000-08-15 | Merck & Co., Inc. | Method of treating cancer |
| FR2775595B1 (en) * | 1998-03-09 | 2000-05-05 | Seppic Sa | SYNERGISTIC COMPOSITION COMPRISING A LIPOAMINOACID STRUCTURE COMPOUND AND MENUPHAR EXTRACT |
| JPH11255715A (en) * | 1998-03-13 | 1999-09-21 | Kao Corp | N,n-di-substituted aniline derivative |
| US20020006418A1 (en) * | 1998-10-13 | 2002-01-17 | John Kung | Composition to enhance permeation of topical skin agents |
| FR2792650B1 (en) * | 1999-04-20 | 2003-02-28 | Oreal | EQUIVALENT OF ELDERLY SKIN, ITS PREPARATION METHOD AND ITS USE |
| KR20020023941A (en) * | 1999-04-30 | 2002-03-29 | 오베르더 왈터 | Antioxidative vitamin b6 analogs |
| EP1176959B1 (en) * | 1999-05-05 | 2006-03-08 | Merck & Co., Inc. | Novel prolines as antimicrobial agents |
| US20020006394A1 (en) * | 2000-02-11 | 2002-01-17 | Redmond Robert W. | Photochemical tissue bonding |
| US6464992B2 (en) * | 2000-04-14 | 2002-10-15 | University Of Kentucky Research Foundation | Topical micronutrient delivery system and uses thereof |
| AU2001272759A1 (en) * | 2000-07-19 | 2002-01-30 | Kyowa Hakko Kogyo Co. Ltd. | Preventives or remedies for atopic dermatitis |
| JP2002128651A (en) * | 2000-10-25 | 2002-05-09 | Kose Corp | Photoaging inhibitor and skin care preparation characterized by comprising the same |
| MXPA03006928A (en) * | 2001-02-05 | 2004-10-15 | Stephen Buchanan Leonard | Multi-tapered dental files. |
| PT1496891E (en) * | 2002-04-19 | 2011-09-02 | Univ Arizona State | Methods for modulating phototoxicity |
| DE102005000868A1 (en) * | 2004-10-15 | 2006-04-20 | Henkel Kgaa | Compositions with inhibitors of prostaglandin and / or leukotriene synthesis in combination with stimulants of the release of cutaneous neuromediators |
-
2003
- 2003-04-17 PT PT03728425T patent/PT1496891E/en unknown
- 2003-04-17 NZ NZ535982A patent/NZ535982A/en not_active IP Right Cessation
- 2003-04-17 ES ES03728425T patent/ES2367258T3/en not_active Expired - Lifetime
- 2003-04-17 CN CNB038087766A patent/CN1298321C/en not_active Expired - Fee Related
- 2003-04-17 US US10/418,629 patent/US6992071B2/en not_active Expired - Lifetime
- 2003-04-17 CA CA2482320A patent/CA2482320C/en not_active Expired - Fee Related
- 2003-04-17 WO PCT/US2003/011842 patent/WO2003088909A2/en active Application Filing
- 2003-04-17 EP EP03728425A patent/EP1496891B1/en not_active Expired - Lifetime
- 2003-04-17 CA CA2668311A patent/CA2668311C/en not_active Expired - Fee Related
- 2003-04-17 DK DK03728425.4T patent/DK1496891T3/en active
- 2003-04-17 AT AT03728425T patent/ATE516802T1/en active
- 2003-04-17 RU RU2004133322/04A patent/RU2301800C2/en not_active IP Right Cessation
- 2003-04-17 AU AU2003234119A patent/AU2003234119B2/en not_active Ceased
- 2003-04-17 JP JP2003585662A patent/JP4527405B2/en not_active Expired - Fee Related
- 2003-04-17 MX MXPA04010228A patent/MXPA04010228A/en active IP Right Grant
-
2004
- 2004-09-09 US US10/937,537 patent/US20050042188A1/en not_active Abandoned
- 2004-10-13 IL IL16456004A patent/IL164560A0/xx unknown
-
2005
- 2005-09-13 US US11/226,615 patent/US7226937B2/en not_active Expired - Lifetime
-
2006
- 2006-01-05 HK HK06100235.9A patent/HK1077761B/en not_active IP Right Cessation
-
2010
- 2010-02-15 IL IL203968A patent/IL203968A/en active IP Right Grant
- 2010-04-28 JP JP2010103731A patent/JP5244150B2/en not_active Expired - Lifetime
-
2011
- 2011-10-14 CY CY20111100977T patent/CY1112194T1/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20220301 |
|
| MKLA | Lapsed |
Effective date: 20200831 |