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1,3-Propane diol esters and ethers and methods for their use in drug delivery
RE40480 1,3-Propane diol esters and ethers and methods for their use in drug delivery
Patent Drawings:

Inventor: Clarkson, et al.
Date Issued: September 2, 2008
Application: 11/405,041
Filed: May 1, 1996
Inventors: Clarkson; Sherri (Douglas, GB)
Manku; Mehar (Hollywood, GB)
Knowles; Philip (Cumbria, GB)
Redden; Peter (Oakville, CA)
Pitt; Andrea (Barnard Castle, GB)
Bradley; Paul (Hathern, GB)
Wakefield; Paul (Cumbria, GB)
McMordie; Austin (Craigavon, GB)
Horrobin; David B. (Guildford, GB)
Assignee: Scarista Limited (Douglas, Isle of Man, GB)
Primary Examiner: Anderson; Rebecca L
Assistant Examiner:
Attorney Or Agent: Buchanan Ingersoll & Rooney PC
U.S. Class: 514/29; 514/420; 548/496; 549/39; 554/227; 554/82; 560/128; 560/38
Field Of Search: 548/496; 549/39; 560/38; 560/128
International Class: C07C 57/13
U.S Patent Documents:
Foreign Patent Documents: 0 018 342; 0 087 864; 0 139 480; 0 139 780; 0161114; 0 173 478; 0 057 797; 0 184 058; 0 056 189; 0 222 155; 0 246 540; 0 161 422; 0319126; 0 321 128; 0 393 920; 0 405 873; 0 405 874; 0 574 312; 0 611 569; 0 675 103; 1 782; 0 888 162; 1 135 647; 1 293 277; 1 493 098; 1 529 762; 1 556 197; 2 161 477; 57-067511; 61-129190; 2-129119; 4-99784; 05-051355; WO 91/09831; WO 94/26262; WO 95/04030; WO 96/33155
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Christie, W.W., et al., "Mass Spectra of the Picolinyl Ester Derivatives of Some Isomeric Dimethylene-Interrupted Octadecadiynoic Acids," Chemical Abstracts, 109:210389(1988). cited by examiner.
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Deterding, L. et al., "Fast-Atom-Bombardment and Tandem Mass Spectrometry for Determining Structures of Fatty Acids and Their Picolyl Ester Derivatives," Chemical Abstracts, VI. 110:38801 (1989). cited by examiner.
Deterding, L., et al., "Tandem Mass Spectrometry for Identifying Fatty Acid Derivatives that Undergo Charge-Remote Fragmentations," Chemical Abstracts 110:56917 (1989). cited by examiner.
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Harvey, D.J., "Pyridine-Containing Derivatives for the Structural Elucidationof the Alkyl Chains of Lipids by Mass Spectrometry and a Comparison with the Spectra of Related Heterocyclic Derivatives," Chemical Abstracts, 114:206360 (1991). cited byexaminer.
Jie, et al., "Mass Spectra of Picolinyl Ester Derivatives of Some Conjugated Diacetylenic Fatty Acids," Chemical Abstracts, 118:191384 (1993). cited by examiner.
Kimura, K. et al., Higher Unsaturated Fatty Alcohol Esters Having Antiucler Activity, Chemical Abstracts, vol. 87, 1997 Abstract No. 53462e. cited by examiner.
Koori, S., "Unsaturated Higher Akuogatuc Esters of Nicotinic Acid," Chemical Abstracts, vol. 77, Abstract No. 164488f (1972). cited by examiner.
Kumokawa, Y. et al. .gamma.-Linolenic Acid Derivatives As Platelet Aggregation Inhibitors, Chemical Abstracts, vol. 105, 1986, Abstract No. 78532f. cited by examiner.
Spitzer, V. et al., "Curupira Tefeensis II: Occurrence of Acetylenic Fatty Acids," Fat Sci. Technol., No. 5, (1991) pp. 169-174. cited by examiner.
Terumo Corp., "Trienoic Fatty Acid Pyridylmethyl Esters," Chemical Abstracts, vol. 101, 1984 Abstract No. 171104v. cited by examiner.









Abstract: The invention relates to compounds of formula: ##STR00001## wherein R.sup.1 is selected from the group consisting of fatty acid acyl groups of 12 to 30 carbon atoms and fatty alcohol groups of 12 to 30 carbon atoms, and wherein R.sup.2 is selected from the group consisting of H, fatty acid acyl of 12 to 30 carbon atoms and fatty alcohol groups of 12 to 30 carbon atoms, the same as or different from R.sup.1, and the residue of a nutrient, drug, or other bioactive compound, and to the use of these compounds to deliver drugs and other bioactive compounds.
Claim: What is claimed is:

.[.1. A compound having the formula:.]. ##STR00004## .[.wherein R.sup.1 is selected from the group consisting of fatty acid acyl groups of 12 to 30 carbon atoms and fattyalcohol groups of 12 to 30 carbon atoms, and wherein R.sup.2 is selected from the group consisting of fatty acid acyl groups of 12 to 30 carbon atoms and fatty alcohol groups of 12 to 30 carbon atoms, the same as or different from R.sup.1, the fatty acidacyl or alcohol groups R.sup.2 being selected from the group consisting of .gamma.-linoleic acid (GLA), dihomo-.gamma.-linolenic acid (DGLA), arachidonic acid (AA), adrenic acid, stearidonic acid (SA), eicosapentaenoic acid (EPA), docosapentaenoic acidn-3, docosahexaenoic acid (DHA), columbinic acid (CA), parinaric acid and conjugated linoleic acid (cLA) groups..].

.[.2. The compound according to claim 1, wherein each said fatty acid or fatty alcohol group has 16 to 30 carbon atoms..].

.[.3. The compound according to claim 1, having a phosphate, succinate, or other difunctional-acid linking moiety between R.sup.1 and the corresponding diol oxygen, between R.sup.2 and the corresponding diol oxygen, or both..].

.[.4. The compound according to claim 1, wherein one of R.sup.1 and R.sup.2 is an acyl moiety corresponding to an acid selected from the group consisting of .gamma.-linolenic acid (GLA) and dihomo-.gamma.-linolenic acid (DGLA), and the other ofR.sup.1 and R.sup.2 is an acyl moiety corresponding to an acid selected from the group consisting of .gamma.-linolenic acid (GLA), dihomo-.gamma.-linolenic acid (DGLA), stearidonic acid (SA), eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA),conjugated linoleic acid (cLA), and columbinic acid (CA)..].

.[.5. The compound according to claim 1, wherein one of R.sup.1 and R.sup.2 is an acyl moiety corresponding to an acid selected from the group consisting of arachidonic acid (AA), and the other is an acyl moiety corresponding to an acidselected from the group consisting of arachidonic acid (AA), .gamma.-linolenic acid (GLA), dihomo-.gamma.-linolenic acid (DGLA), docosahexaenoic acid (DHA), and eicosapentaenoic acid (EPA)..].

.[.6. The compound according to claim 1, wherein one of the R.sup.1 and R.sup.2 is an acyl moiety corresponding to eicosapentaenoic acid (EPA) and the other is an acyl moiety corresponding to an acid selected from the group consisting ofeicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA)..].

.[.7. A pharmaceutical composition comprising an effective amount of the compound of claim 1 and a suitable diluent or carrier..].

.[.8. A compound according to claim 1 having the following 1,3-propane diol linked structure:.]. ##STR00005## .[.wherein R.sup.1 and R.sup.2 are pairs of fatty acids selected from the group of pairs of fatty acids consisting of:.gamma.-linolenic acid and oleic acid; .gamma.-linolenic acid and .gamma.-linolenic acid; eicosapentaenoic acid and eicosapentaenoic acid; .gamma.-linolenic acid and eicosapentaenoic acid; .gamma.-linolenic acid and docosahexaenoic acid; arachidonicacid and docosahexaenoic acid; arachidonic acid and eicosapentaenoic acid; .gamma.-linolenic acid and arachidonic acid; .gamma.-linolenic acid and stearidonic acid; stearidonic acid and docosahexaenoic acid; arachidonic acid and stearidonic acid; dihomo-.gamma.-linolenic acid and dihomo-.gamma.-linolenic acid; dihomo-.gamma.-linolenic acid and .gamma.-linolenic acid; dihomo-.gamma.-linolenic acid and stearidonic acid; dihomo-.gamma.-linolenic acid and arachidonic acid; dihomo-.gamma.-linolenic acid and eicosapentaenoic acid; dihomo-.gamma.-linolenic acid and docosahexaenoic acid; arachidonic acid and arachidonic acid; eicosapentaenoic acid and stearidonic acid; eicosapentaenoic acid and docosahexaenoic acid; docosahexaenoic acid and docosahexaenoic acid; conjugated linoleic acid and conjugated inoleic acid, conjugated linoleic acid and .gamma.-linolenic acid; conjugated linoleic acid and dihomo-.gamma.-linolenic acid; conjugated linoleic acid andarachidonic acid; conjugated hinoleic acid and stearidonic acid; conjugated linoleic acid and eicosapentaenoic acid; conjugated linoleic acid and docosahexaenoic acid; columbinic acid and columbinic acid; columbinic acid and .gamma.-linolenic acid; columbinic acid and dihomo-.gamma.-linolenic acid; columbinic acid and arachidonic acid; columbinic acid and stearidonic acid; columbinic acid and eicosapentaenoic acid; and columbinic acid and docosahexaenoic acid..].

.[.9. The compound according to claim 8, wherein R.sup.1 and R.sup.2 are both docosahexaenoic acid moieties..].

.[.10. The compound according to claim 8, wherein R.sup.1 and R.sup.2 are both eicosapentaenoic acid moieties..].

.[.11. A pharmaceutical composition comprising an effective amount of the compound of 8, 9 or 10 and a suitable diluent or carrier..].

.Iadd.12. A compound having the formula: R.sup.1OCH.sub.2--CH.sub.2--CH.sub.2OR.sup.2 wherein R.sup.1 is selected from the group consisting of fatty acid acyl groups of 12 to 30 carbon atoms and fatty alcohol groups of 12 to 30 carbon atoms,and wherein R.sup.2 is lipoic acid..Iaddend.

.Iadd.13. A compound having the formula: R.sup.1OCH.sub.2--CH.sub.2--CH.sub.2OR.sup.2 wherein R.sup.1 is selected from the group consisting of fatty acid acyl groups of 12 to 30 carbon atoms and fatty alcohol groups of 12 to 30 carbon atoms,and wherein R.sup.2 is a tryptophan, phenylalanine, GABA, fluoextine, or tranylcypromine moiety..Iaddend.

.Iadd.14. The compound according to claim 13, wherein R.sup.1 is is .gamma.-linolenic acid (GLA) and R.sup.2 is tryptophan..Iaddend.

.Iadd.15. The compound according to claim 13, wherein R.sup.1 is is .gamma.-linolenic acid (GLA) and R.sup.2 is phenylalanine..Iaddend.

.Iadd.16. The compound according to claim 13, wherein R.sup.1 is is .gamma.-linolenic acid (GLA) and R.sup.2 is GABA..Iaddend.

.Iadd.17. The compound according to claim 15, wherein R.sup.1 is is .gamma.-linolenic acid (GLA) and R.sup.2 is phenylalanine..Iaddend.

.Iadd.18. The compound according to claim 15, wherein R.sup.1 is is .gamma.-linolenic acid (GLA) and R.sup.2 is GABA..Iaddend.
Description:
 
 
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