CA2400462A1 - Aspirin-triggered lipid mediators - Google Patents

Aspirin-triggered lipid mediators Download PDF

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Publication number
CA2400462A1
CA2400462A1 CA002400462A CA2400462A CA2400462A1 CA 2400462 A1 CA2400462 A1 CA 2400462A1 CA 002400462 A CA002400462 A CA 002400462A CA 2400462 A CA2400462 A CA 2400462A CA 2400462 A1 CA2400462 A1 CA 2400462A1
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hydrogen atom
compound
pharmaceutically acceptable
prodrug
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CA002400462A
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CA2400462C (en
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Charles N. Serhan
Clary B. Clish
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Brigham and Womens Hospital Inc
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Brigham And Women's Hospital, Inc.
Charles N. Serhan
Clary B. Clish
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    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
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    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
    • C12P7/6409—Fatty acids
    • C12P7/6427—Polyunsaturated fatty acids [PUFA], i.e. having two or more double bonds in their backbone
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    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
    • C12P7/6436—Fatty acid esters
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    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
    • C12P7/6436—Fatty acid esters
    • C12P7/6445—Glycerides
    • C12P7/6472—Glycerides containing polyunsaturated fatty acid [PUFA] residues, i.e. having two or more double bonds in their backbone
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

Aspirin triggered lipid mediators (ATLMs) are disclosed which are useful for the treatment or prevention of inflammation associated with various diseases , including ischemia.

Claims (39)

1. A compound having the formula:
wherein R is a hydrogen atom or a pharmaceutically acceptable salt, ester, amide or prodrug and wherein P is a hydrogen atom or a protecting group.
2. The compound of claim 1, wherein the C-15 carbon has an R configuration.
3. The compound of claim 1, wherein the C-15 carbon has an S configuration.
4. A compound having the formula:
wherein R is a hydrogen atom or a pharmaceutically acceptable salt, ester, amide or prodrug and wherein P is a hydrogen atom or a protecting group.
5. The compound of claim 4, wherein the C-18 carbon has an R configuration.
6. The compound of claim 4, wherein the C-18 carbon has an S configuration.
7. A compound having the formula:
wherein R is a hydrogen atom or a pharmaceutically acceptable salt, ester, amide or prodrug and wherein one or more P's are hydrogen atoms or one or more protecting groups or combinations thereof.
8. The compound of claim 7, wherein the C-5 carbon has an S configuration, the C-12 carbon has an R configuration and the C-18 carbon has an R
configuration.
9. A compound having the formula:
wherein R is a hydrogen atom or a pharmaceutically acceptable salt, ester, amide or prodrug and wherein one or more P's are hydrogen atoms or protecting groups or combinations thereof.
10. The compound of claim 9, wherein the C-5 carbon has an S configuration, the C-6 carbon has an R configuration and the C-15 carbon has an R
configuration.
11. A method for treating or preventing inflammation in a subject, comprising the step of administering a combination of an omega-3 fatty acid and aspirin, such that inflammation is treated or prevented in the subject.
12. The method of claim 1 l, wherein the omega-3 fatty acid and aspirin are administered at two different times.
13. The method of claim 11, wherein the omega-3 fatty acid is eicosapentanoic acid.
14. The method of claim 11, wherein the omega-3 fatty acid is docosahexaenoic acid.
15. A method for treating arterial inflammation, arthritis, or cardiovascular diseases in a subject, comprising the step of administering to the subject a combination of an omega-3 fatty acid and aspirin, such that arterial inflammation, arthritis, or cardiovascular disease is treated or prevented in the subject.
16. The method of claim 15, wherein the omega-3 fatty acid and aspirin are administered at two different times.
17. The method of claim 15, wherein the omega-3 fatty acid is eicosapentanoic acid.
18. The method of claim 15, wherein the omega-3 fatty acid is docosahexaenoic acid.
19. A method for treating or preventing inflammation in a subject, comprising the step of administering to the subject a compound having the formula:
wherein R is a hydrogen atom or is a pharmaceutically acceptable salt, ester, amide or prodrug and wherein P is a hydrogen atom or a protecting group, such that inflammation is treated or prevented in the subject.
20. A method for treating or preventing inflammation in a subject, comprising the step of administering to the subject a compound having the formula:
wherein R is a hydrogen atom or a pharmaceutically acceptable salt, ester, amide or prodrug and wherein P is a hydrogen atom or a protecting group, such that inflammation is treated or prevented in the subject.
21. A method for treating or preventing inflammation in a subject, comprising the step of administering to the subject a compound having the formula:
wherein R is a hydrogen atom or a pharmaceutically acceptable salt, ester, amide or prodrug and wherein one or more P's are hydrogen atoms or one or more protecting groups or combinations thereof, such that inflammation is treated or prevented in the subject.
22. A method for treating or preventing inflammation in a subject, comprising the step of administering to the subject a compound having the formula:

wherein R is a hydrogen atom or a pharmaceutically acceptable salt, ester, amide or prodrug and wherein one or more P's are hydrogen atoms or one or more protecting groups or combinations thereof, such that inflammation is treated or prevented in the subject.
23. A method for treating arterial inflammation, arthritis, or cardiovascular diseases in a subject, comprising the step of administering to the subject compound having the formula:
wherein R is a hydrogen atom or a pharmaceutically acceptable salt, ester, amide or prodrug and wherein P is a hydrogen atom or a protecting group, such that arterial inflammation, arthritis, or cardiovascular disease is treated or prevented in the subject.
24. A method for treating arterial inflammation, arthritis, or cardiovascular diseases in a subject, comprising administering to the subject a compound having the formula:

wherein R is a hydrogen atom or a pharmaceutically acceptable salt, ester, amide or prodrug and P is a hydrogen atom or a protecting group, such that arterial inflammation, arthritis, or cardiovascular disease is treated or prevented in the subject.
25. A method for treating arterial inflammation, arthritis, or cardiovascular diseases in a subject, comprising administering to the mammal a compound having the formula:

wherein R is a hydrogen atom or a pharmaceutically acceptable salt, ester, amide or prodrug and wherein one or more P's are hydrogen atoms or one or more protecting groups or combinations thereof, such that arterial inflammation, arthritis, or cardiovascular disease is treated or prevented in the subject.
26. A method for treating arterial inflammation, arthritis, or cardiovascular diseases in a subject, comprising administering to the mammal a compound having the formula:

wherein R is a hydrogen atom or a pharmaceutically acceptable salt, ester, amide or prodrug and wherein one or more P's are hydrogen atoms or one or more protecting groups or combinations thereof, such that arterial inflammation, arthritis, or cardiovascular disease is treated or prevented in the subject.
27. A hydroxyl protected or unprotected monohydroxyl-docosahexaenoic acid or a pharmaceutically acceptable analogue thereof.
28. A compound having the formula:

wherein R is a hydrogen atom or a pharmaceutically acceptable salt, ester, amide or prodrug and wherein P is a hydrogen atom or a protecting group.
29. A compound having the formula:

wherein R is a hydrogen atom or a pharmaceutically acceptable salt, ester, amide or prodrug and wherein P is a hydrogen atom or a protecting group.
30. A compound having the formula:

wherein R is a hydrogen atom or a pharmaceutically acceptable salt, ester, amide or prodrug and wherein P is a hydrogen atom or a protecting group.
31. A compound having the formula:

wherein R is a hydrogen atom or a pharmaceutically acceptable salt, ester, amide or prodrug and wherein P is a hydrogen atom or a protecting group.
32. A compound having the formula:

wherein R is a hydrogen atom or a pharmaceutically acceptable salt, ester, amide or prodrug and wherein P is a hydrogen atom or a protecting group.
33. A compound having the formula:

wherein R is a hydrogen atom or a pharmaceutically acceptable salt, ester, amide or prodrug and wherein P is a hydrogen atom or a protecting group.
34. A method for treating or preventing inflammation in a subject, comprising the step of administering to the subject a compound having the formula:

wherein R is a hydrogen atom or a pharmaceutically acceptable salt, ester, amide or prodrug and wherein P is a hydrogen atom or a protecting group, such that the subject is treated.
35. A method for treating or preventing inflammation in a subject, comprising the step of administering to the subject a compound having the formula:

wherein R is a hydrogen atom or a pharmaceutically acceptable salt, ester, amide or prodrug and wherein P is a hydrogen atom or a protecting group, such that the subject is treated.
36. A method for treating or preventing inflammation in a subject, comprising the step of administering to the subject a compound having the formula:

wherein R is a hydrogen atom or a pharmaceutically acceptable salt, ester, amide or prodrug and wherein P is a hydrogen atom or a protecting group, such that the subject is treated.
37. A method for treating or preventing inflammation in a subject, comprising the step of administering to the subject a compound having the formula:

wherein R is a hydrogen atom or a pharmaceutically acceptable salt, ester, amide or prodrug and wherein P is a hydrogen atom or a protecting group, such that the patient is treated.
38. A method for treating or preventing inflammation in a subject, comprising the step of administering to the subject a compound having the formula:

wherein R is a hydrogen atom or a pharmaceutically acceptable salt, ester, amide or prodrug and wherein P is a hydrogen atom or a protecting group, such that the subject is treated.
39. A method for treating or preventing inflammation in a subject, comprising the step of administering to the subject a compound having the formula:

wherein R is a hydrogen atom or a pharmaceutically acceptable salt, ester, amide or prodrug and wherein P is a hydrogen atom or a protecting group, such that the subject is treated.
CA2400462A 2000-02-16 2001-02-16 Aspirin-triggered lipid mediators Expired - Lifetime CA2400462C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US18307800P 2000-02-16 2000-02-16
US60/183,078 2000-02-16
US23881400P 2000-10-06 2000-10-06
US60/238,814 2000-10-06
PCT/US2001/005196 WO2001060778A2 (en) 2000-02-16 2001-02-16 Aspirin-triggered lipid mediators

Publications (2)

Publication Number Publication Date
CA2400462A1 true CA2400462A1 (en) 2001-08-23
CA2400462C CA2400462C (en) 2011-09-27

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CA2400462A Expired - Lifetime CA2400462C (en) 2000-02-16 2001-02-16 Aspirin-triggered lipid mediators

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US (5) US6670396B2 (en)
EP (2) EP1762557B1 (en)
JP (5) JP4932116B2 (en)
CN (4) CN102010324B (en)
AT (2) ATE344226T1 (en)
AU (4) AU2001238468B2 (en)
CA (1) CA2400462C (en)
DE (2) DE60144401D1 (en)
HK (1) HK1105948A1 (en)
IL (1) IL151299A0 (en)
MX (1) MXPA02007915A (en)
WO (1) WO2001060778A2 (en)

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