IP Library Granted Patent US 12,599,580
Granted Patent B2
US 12,599,580 · App. 17/737,761 · Granted Apr 14, 2026

Composition comprising a lipid compound, a triglyceride, and a surfactant, and methods of using the same

Inventors: Svein Olaf Hustvedt (Olso, NO); Preben Houlberg Olesen (København NV, DK); Annette Müllertz (Charlottenlund, DK)
Assignee: BASF AS
A61K31/202A61K9/0053A61K9/107A61K9/48A61K31/20A61K47/10A61K47/14A61K47/26
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,599,580
App. No.
17/737,761
Granted
Apr 14, 2026
Kind
B2
Abstract

Compositions comprising 2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenyloxy)butanoic acid, an ester derivative, or a pharmaceutically acceptable salt thereof; a triglyceride; and a surfactant, as well as methods for their use. The present disclosure further relates to self-emulsifying drug delivery systems, such as SEDDS, SMEDDS, or SNEDDS comprising 2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenyloxy)butanoic acid.

Claims (28)

1 . A method for the treatment of a disease or condition chosen from:

a dyslipidemic condition; and/or

elevated triglyceride levels, non-HDL cholesterol levels, LDL cholesterol levels, and/or VLDL cholesterol levels; in a subject in need thereof, comprising administering to the subject a pharmaceutically active amount of a composition comprising from 5% to 60% by weight of the total composition of 2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenyloxy)butanoic acid, and ester derivative, or a pharmaceutically acceptable salt thereof;

from 15% to 60% by weight of the total composition of a medium-chain triglyceride (MCT) oil; and

from 10% to 60% by weight of the total composition of a nonionic surfactant.

2 . The method according to claim 1 , wherein the dyslipidemic condition is chosen from hypertriglyceridemia (HTG), dyslipidemia, and mixed dyslipidemia.

3 . A method for the treatment of a disease or condition chosen from an inflammatory disease or condition and/or atherosclerosis in a subject in need thereof, comprising administering to the subject a pharmaceutically active amount of a composition comprising from 5% to 60% by weight of the total composition of 2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenyloxy)butanoic acid, and ester derivative, or a pharmaceutically acceptable salt thereof;

from 15% to 60% by weight of the total composition of a medium-chain triglyceride (MCT) oil; and

from 10% to 60% by weight of the total composition of a nonionic surfactant.

4 . A method for the treatment of a disease or condition chosen from peripheral insulin resistance, a diabetic condition, and/or type 2 diabetes in a subject in need thereof, comprising administering to the subject a pharmaceutically active amount of a composition comprising from 5% to 60% by weight of the total composition of 2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenyloxy)butanoic acid, and ester derivative, or a pharmaceutically acceptable salt thereof;

from 15% to 60% by weight of the total composition of a medium-chain triglyceride (MCT) oil; and

from 10% to 60% by weight of the total composition of a nonionic surfactant.

5 . The method according to claim 1 , wherein the total dose of 2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenyloxy)butanoic acid, an ester derivative, or a pharmaceutically acceptable salt thereof, administered per day as a total dose ranges from about 50 mg to about 800 mg.

6 . The method according to claim 3 , wherein the total dose of 2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenyloxy)butanoic acid, an ester derivative, or a pharmaceutically acceptable salt thereof, administered per day as a total dose ranges from about 50 mg to about 800 mg.

7 . The method according to claim 4 , wherein the total dose of 2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenyloxy)butanoic acid, an ester derivative, or a pharmaceutically acceptable salt thereof, administered per day as a total dose ranges from about 50 mg to about 800 mg.

8 . The method according to claim 1 , wherein the composition is administered once daily.

9 . The method according to claim 3 , wherein the composition is administered once daily.

10 . The method according to claim 4 , wherein the composition is administered once daily.

11 . The method according to claim 1 , wherein the medium chain triglyceride oil consists essentially of C 8 -C 10 triglycerides.

12 . The method according to claim 1 , wherein the medium chain triglyceride oil is derived from capric acid and caprylic acid.

13 . The method according to claim 3 , wherein the medium chain triglyceride oil consists essentially of C 8 -C 10 triglycerides.

14 . The method according to claim 3 , wherein the medium chain triglyceride oil is derived from capric acid and caprylic acid.

15 . The method according to claim 4 , wherein the medium chain triglyceride oil consists essentially of C 8 -C 10 triglycerides.

16 . The method according to claim 4 , wherein the medium chain triglyceride oil is derived from capric acid and caprylic acid.

17 . The method according to claim 1 , wherein the nonionic surfactant is chosen from polyoxyethylene (20) sorbitan monooleate with an HLB value of 15.0 (TWEEN 80) and polyoxyethylene (20) sorbitan monolaurate with an HLB value of 16.0 (TWEEN 20).

18 . The method according to claim 3 , wherein the nonionic surfactant is chosen from polyoxyethylene (20) sorbitan monooleate with an HLB value of 15.0 (TWEEN 80) and polyoxyethylene (20) sorbitan monolaurate with an HLB value of 16.0 (TWEEN 20).

19 . The method according to claim 4 , wherein the nonionic surfactant is chosen from polyoxyethylene (20) sorbitan monooleate with an HLB value of 15.0 (TWEEN 80) and polyoxyethylene (20) sorbitan monolaurate with an HLB value of 16.0 (TWEEN 20).

20 . The method according to claim 2 , wherein the wherein the medium chain triglyceride oil is derived from capric acid and caprylic acid and the nonionic surfactant is chosen from polyoxyethylene (20) sorbitan monooleate with an HLB value of 15.0 (TWEEN 80) and polyoxyethylene (20) sorbitan monolaurate with an HLB value of 16.0 (TWEEN 20).

Assignments (2)
MERGER AND CHANGE OF NAME Recorded Jan 9, 2026
From: BASF AND PRONOVA BIOPHARMA NORGE AS; BASF AS
To: BASF AS
Reel/Frame 073422/0467 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 9, 2026
From: HUSTVEDT, SVEIN O.; OLESEN, PREBEN H.; MULLERTZ, ANNETTE
To: PRONOVA BIOPHARMA NORGE AS
Reel/Frame 074295/0294 →
Continuity (3)
Division 14770862
Provisional Application 61770646 · Feb 28, 2013
Related Publication 20230090432A1 · Mar 23, 2023
References Cited (244)
US 2909554A · Doerr · 1959 [cited by applicant]
US 4009211A · Onopchenko et al. · 1977 [cited by applicant]
US 4032564A · Henrick et al. · 1977 [cited by applicant]
US 4040781A · Lamberti et al. · 1977 [cited by applicant]
US 4209410A · Baldwin · 1980 [cited by applicant]
US 4214088A · Abeler et al. · 1980 [cited by applicant]
US 4286053A · Ishikawa et al. · 1981 [cited by applicant]
US 4297268A · Abeler et al. · 1981 [cited by applicant]
US 4368190A · Shen et al. · 1983 [cited by applicant]
US 4411808A · Gutierrez et al. · 1983 [cited by applicant]
US 4444766A · Bosies et al. · 1984 [cited by applicant]
US 4652441A · Okada et al. · 1987 [cited by applicant]
US 5306754A · Yamamoto et al. · 1994 [cited by applicant]
US 5328953A · Lynch · 1994 [cited by applicant]
US 5445832A · Orsolini et al. · 1995 [cited by applicant]
US 5447820A · Hayakawa et al. · 1995 [cited by applicant]
US 5523430A · Patel et al. · 1996 [cited by applicant]
US 5612093A · Braig et al. · 1997 [cited by applicant]
US 5763517A · Yamamoto et al. · 1998 [cited by applicant]
US 5770584A · Kucera · 1998 [cited by applicant]
US 5990173A · Patoiseau et al. · 1999 [cited by applicant]
US 6060515A · Elias et al. · 2000 [cited by applicant]
US 6087353A · Stewart · 2000 [cited by applicant]
US 6284268B1 · Mishra · 2001 [cited by applicant]
US 6365628B1 · Berge · 2002 [cited by applicant]
US 6376688B1 · Ferrante et al. · 2002 [cited by applicant]
US 6511670B1 · Maignan et al. · 2003 [cited by applicant]
US 6624190B2 · Khoury et al. · 2003 [cited by applicant]
US 6723717B1 · Youngquist et al. · 2004 [cited by applicant]
US 6835750B1 · Henderson · 2004 [cited by applicant]
US 7250456B2 · Eigen et al. · 2007 [cited by applicant]
US 7273852B2 · Tsuji et al. · 2007 [cited by applicant]
US 7427583B2 · Couillet et al. · 2008 [cited by applicant]
US 7517858B1 · Hostetler et al. · 2009 [cited by applicant]
US 7902399B2 · Berge et al. · 2011 [cited by applicant]
US 7968617B2 · Thalacker et al. · 2011 [cited by applicant]
US 8173831B2 · Milne et al. · 2012 [cited by applicant]
US 8304551B2 · Milne et al. · 2012 [cited by applicant]
US 8735436B2 · Hovland et al. · 2014 [cited by applicant]
US 8741966B2 · Holmeide · 2014 [cited by applicant]
US 8759558B2 · Holmeide et al. · 2014 [cited by applicant]
US 8946190B2 · Gagnon · 2015 [cited by applicant]
US 9394228B2 · Hovland et al. · 2016 [cited by applicant]
US 20020156124A1 · Gao · 2002 [cited by applicant]
US 20030147814A1 · Scherrer et al. · 2003 [cited by applicant]
US 20040126424A1 · Jandacek et al. · 2004 [cited by applicant]
US 20050107503A1 · Couillet et al. · 2005 [cited by applicant]
US 20060135785A1 · Patoiseau et al. · 2006 [cited by applicant]
US 20060247458A1 · Yamamoto et al. · 2006 [cited by applicant]
US 20060251685A1 · Yu · 2006 [cited by applicant]
US 20070060497A1 · Krahmer et al. · 2007 [cited by applicant]
US 20070088170A1 · Bryhn et al. · 2007 [cited by applicant]
US 20070167529A1 · Walton et al. · 2007 [cited by applicant]
US 20070254026A1 · Stewart · 2007 [cited by applicant]
US 20070254862A1 · Antel et al. · 2007 [cited by applicant]
US 20080124387A1 · Spilburg · 2008 [cited by applicant]
US 20080317844A1 · Dudley · 2008 [cited by applicant]
US 20090137567A1 · Perrine et al. · 2009 [cited by applicant]
US 20100267828A1 · Holmeide et al. · 2010 [cited by applicant]
US 20100280109A1 · Holmeide · 2010 [cited by applicant]
US 20110054029A1 · Kuhrts · 2011 [cited by applicant]
US 20110190395A1 · Holmeide et al. · 2011 [cited by applicant]
US 20120122940A1 · Hovland et al. · 2012 [cited by applicant]
US 20120252850A1 · Milne et al. · 2012 [cited by applicant]
US 20120264791A1 · Milne et al. · 2012 [cited by applicant]
US 20130046013A1 · Hovland et al. · 2013 [cited by applicant]
US 20130345269A1 · Hovland et al. · 2013 [cited by applicant]
US 20140221439A1 · Hovland et al. · 2014 [cited by applicant]
US 20140316002A1 · Holmeide et al. · 2014 [cited by applicant]
US 20160206585A1 · Hustvedt et al. · 2016 [cited by applicant]
CA 2115345 · 1993 [cited by applicant]
CA 2667211A1 · 2008 [cited by applicant]
CA 2667150A1 · 2008 [cited by applicant]
CN 1248916A · 2000 [cited by applicant]
CN 101213281A · 2008 [cited by applicant]
CN 101225064 · 2008 [cited by applicant]
CN 1024241422A · 2012 [cited by applicant]
CN 102459142A · 2012 [cited by applicant]
CN 101213281B · 2013 [cited by applicant]
EP 0002007 · 1979 [cited by applicant]
EP 0050327 · 1982 [cited by applicant]
EP 0052510A3 · 1982 [cited by applicant]
EP 0175591 · 1986 [cited by applicant]
EP 0346879A1 · 1989 [cited by applicant]
EP 0399183 · 1990 [cited by applicant]
EP 0463947 · 1992 [cited by applicant]
EP 2248798 · 2010 [cited by applicant]
ES 2009346 · 1989 [cited by applicant]
GB 1038723 · 1966 [cited by applicant]
GB 1393805 · 1975 [cited by applicant]
GB 1523276A · 1978 [cited by applicant]
GB 2209937A · 1989 [cited by applicant]
JP 48039001B · 1973 [cited by applicant]
JP 04051149 · 1992 [cited by applicant]
JP 11180929 · 1999 [cited by applicant]
JP 2000344736A · 2000 [cited by applicant]
JP 2003527364T · 2003 [cited by applicant]
JP 2009520797A · 2009 [cited by applicant]
JP 2014505017A · 2014 [cited by applicant]
TW 201233388A · 2012 [cited by applicant]
WO WO9611908A · 1996 [cited by applicant]
WO WO199738688 · 1997 [cited by applicant]
WO WO98032444 · 1998 [cited by applicant]
WO WO199916804 · 1999 [cited by applicant]
WO WO00072920 · 2000 [cited by applicant]
WO WO0168582 · 2001 [cited by applicant]
WO WO01098328 · 2001 [cited by applicant]
WO WO03014073 · 2003 [cited by applicant]
WO WO03063878 · 2003 [cited by applicant]
WO WO2005073164 · 2005 [cited by applicant]
WO WO2006025246 · 2006 [cited by applicant]
WO WO2006094915 · 2006 [cited by applicant]
WO WO2006117664A1 · 2006 [cited by applicant]
WO WO2006117668A1 · 2006 [cited by applicant]
WO WO2007072061A2 · 2007 [cited by applicant]
WO WO2007116027 · 2007 [cited by applicant]
WO WO2008053331 · 2008 [cited by applicant]
WO WO2008053340 · 2008 [cited by applicant]
WO WO2008125241 · 2008 [cited by applicant]
WO WO2009056983 · 2009 [cited by applicant]
WO WO2009061208 · 2009 [cited by applicant]
WO WO2009149496 · 2009 [cited by applicant]
WO WO2009156621 · 2009 [cited by applicant]
WO WO2010006085 · 2010 [cited by applicant]
WO WO2010008299 · 2010 [cited by applicant]
WO WO2010103402A1 · 2010 [cited by applicant]
WO WO2010103404A1 · 2010 [cited by applicant]
WO WO2010128401 · 2010 [cited by examiner]
WO WO2010128401A1 · 2010 [cited by applicant]
WO WO2011089529 · 2011 [cited by applicant]
WO WO2012032415A2 · 2012 [cited by applicant]
WO WO2012059818A1 · 2012 [cited by applicant]
WO WO2012115695 · 2012 [cited by applicant]
WO WO2013016531 · 2013 [cited by applicant]
Ahmad, J. et al., “Reactions in Monolayers: Base-Catalyzed Ester Hydrolysis Revisited,” Langmuir (1990) 6:1797-1799. [cited by applicant]
Anby, M. et al., “Lipid Digestion as a Trigger for Supersaturation: Evaluation of the Impact of Supersaturation Stabilization on the in Vitro and in Vivo Performance of Self-Emulsifying Drug Delivery Systems,” Molecular… [cited by applicant]
Bach et al. (The American Journal of Clinical Nutrition 36: Nov. 1982, pp. 950-962). [cited by applicant]
Berge et al., “Metabolic effects ofthia fatty acids.” Current Opinion in Lipidology. (2002) 13(3): 295-304. [cited by applicant]
Berge, S.M et al., “Pharmaceutical Salts,” J. Pharmaceutical Sciences (1977) 66(1):1-19. [cited by applicant]
Brain, E.G et al., “Derivatives of 6-Aminopenicillanic Acid. Part II.” Trisubstituted Acetyl Derivatives, J. Chemical Society (1962) 1445-1453. [cited by applicant]
Burness, D.M. “Decarboxylation of Thietin Salts,” J. Organic Chemistry, (1959) 24(6):849-852. [cited by applicant]
Buyukozturk, F. et al., “Impact of emulsion-based drug delivery systems on intestinal permeability and drug release kinetics,” Journal of Controlled Release, 201 O; 142: 22-30. [cited by applicant]
Cao, G. Selected topics of pharmaceutical chemistry. China Medical Science Press, 1993. pp. 123-125. [cited by applicant]
Chen, et al. Basic Drug Design, 1st Edition, Huazhong University of Science and Technology (HUST) Press, 1995, pp. 162-169. [cited by applicant]
Derzhinskii, A.R. et al., “Functional Sulfur-Containing Compounds. Part 4. Preparation of Chloro(Bromo) Alkyl Sulfones by Oxidative Halogenation of Hydroxyalkyl Sulfides and Sulfoxides with Mixtures of Hydrogen Peroxide… [cited by applicant]
English language abstract for CN 101225064. [cited by applicant]
English language abstract for CN 102421422. [cited by applicant]
English language abstract for CN 102459142. [cited by applicant]
English language abstract for EP O 463 947. [cited by applicant]
English language abstract for JP 04-051149. [cited by applicant]
English language abstract of ES 2 009 346, Sep. 16, 1989. [cited by applicant]
English language translation of Microcarrier Drug Delivery System, Huazhong University of Science and Technology Press, (ed. Cheng Fang), copyright 2009, pp. 217-219 (8 pages). [cited by applicant]
English machine translation of JP 11-180929. [cited by applicant]
English translation of JP 48-039001 B. [cited by applicant]
English translation, Cao, G. Selected topics of pharmaceutical chemistry. China Medical Science Press, 1993. pp. 123-125. [cited by applicant]
English translation, Chen, et al. Basic Drug Design, 1st Edition (Huazhong University of Science and Technology (HUST) Press, 1995), p. 162-169. [cited by applicant]
English Translation, Silverman, R.B., The Organic Chemistry of Drug Design and Drug Action, 2nd Edition, 19-20, (Chemical Industry Press, 2008). [cited by applicant]
Ferrell, W.J., “Synthesis and Properties of 35S, 14C and 3H Labeled S-Alkyl Glycerol Ethers and Derivatives,” Chemistry and Physics of Lipids (1976) 16:276-284. [cited by applicant]
Ferrucci, L. et al., “Relationship of Plasma Polyunsaturated Fatty Acids to Circulating Inflammatory Markers,” J. Clin. Endocrin. & Metab. (2006) 91 (2):439-446. [cited by applicant]
Flock et al., “Syntheses of Some Polyunsaturated Sulfur- and Oxygen-Containing Fatty Acids Related to Eicosapentaenoic and Docosahexaenoic Acids,” Acta Chemica Scandinavica (1999) 53:436-445. [cited by applicant]
Geleijnse, J.M. et al., “Blood Pressure Response to Fish Oil Supplementation: Metaregression Analysis of Randomized Trials,” J. Hypertension (2002) 20(8):1493-1499. [cited by applicant]
Goldsworthy, L.J. et al., “Some Sulphides Containing the 2-Chloroethyl Group,” Journal of the Chemical Society (1948) 2177-2179. [cited by applicant]
Granlund, L. et al., “Effects of Structural Changes of Fatty Acids on Lipid Accumulation in Adipocytes and Primary Hepatocytes,” Biochemica et Biophysica Acta (2005) 1687:23-30. [cited by applicant]
Grupp, I.L. et al., “Protection Against Hypoxia-Reoxygenation in the Absence of Poly (ADP-Ribose) Synthetase in Isolated Working Hearts,” J. Mol. Cell Cardiol. (1999) 31 :297-303. [cited by applicant]
Heckmann, B. et al., “Grignard Additions to a,!3-Unsaturated Dioxolanones: Preparation of Chiral Allyic Alcohols and Protected a-Hydroxy Aldehydes,” Tetrahedron Letters (1996) 37:1421-1424. [cited by applicant]
Hermetter, A. & Pal Tauf, F., “A Facile Procedure for the Synthesis of Saturated Phosphatidylcholines,” Chemistry & Physics of Lipids (1981) 28: 111-115. [cited by applicant]
Hernandez, V. A et al., “Thiazolidinediones and Risk of Heart Failure in Patients with or at High Risk or Type 2 Diabetes Mellitus,” Am J Cardiovasc Drugs 2011; 11 (2) pp. 115-128. [cited by applicant]
Hill, A.J. & Fager, E.W., “Some a-Alkylthio Aliphatic Acids,” Journal of the American Chemical Society (1943) 65(12):2300-2301. [cited by applicant]
Holmeide, A.K. & Skattenbol, L., “Syntheses of Some Polyunsaturated Trifluoromethyl Ketones as Potential Phospholipase A2 Inhibitors,” J. Chem. Soc., Perkin Trans. (2000) 1 :2271-2276. [cited by applicant]
Hosokawa, M. et al., “Preparation of Therapeutic Phospholipids Through Porcine Pancreatic Phospholipase A2-Mediated Esterification and Lipozyme-Mediated Acidolysis,” J. Am. Oil Chem. Soc. (1995) 72(11):1287-1291. [cited by applicant]
International Search Report for International Application No. PCT/IB2010/001251, dated Oct. 4, 2010. [cited by applicant]
International Search Report for International Application No. PCT/IB2011/000250, dated May 31, 2011. [cited by applicant]
International Search Report for International Application No. PCT/IB2011/002925, dated Mar. 5, 2012. [cited by applicant]
International Search Report for International Application No. PCT/NO2008/000391, dated Feb. 4, 2009. [cited by applicant]
International Search Report for International Application No. PCT/NO2009/000262, dated Oct. 23, 2009. [cited by applicant]
International Search Report of International Application No. PCT/IB2014/000823, Jul. 17, 2014. [cited by applicant]
Jones, P.B. et al., “A New Class of Antituberculosis Agents,” J. Med. Chem. (2003) 43: 3304-3314. [cited by applicant]
Kameyama, E. et al., “Alkylcarboxymethyl Sulphoxides,” American Chemical Society Chemical Abstracts (1971) 7 4(23):401. [cited by applicant]
Kasai, Y. et al., “Synthesis of Diphenylalkane Sulfonate and Its Surface Activity,” Yes Kogyo Kagaku Zasshi (1965) 68(11):2073-2077. [cited by applicant]
Lamango, N.S. et al., “Inhibition Mechanism of S-Adenosylmethionine-Induced Movement Deficits by Prenylcysteine Analogs,” Pharmacology, Biochemistry, & Behavior (2003) 43:433-442. [cited by applicant]
Larsen et al., “a- and Is- Alkyl-Substituted Eicosapentaenoic Acids: Incorporation into Phospholipids and Effects on Prostaglandin H Synthase and 5-Lipoxygenase,” Biochemical Pharmacology (1998) 55:405-11. [cited by applicant]
Larsen, L.N. et al., “Polyunsaturated Thia- and Oxa-Fatty Acids: Incorporation into Cell-Lipids and Their Effects on Arachidonic Acid- and Eicosanoid Syntheses,” Biochemica et Biophysica Acta (1997) 1348:346-354. [cited by applicant]
Larsen, L.N. et al., “Sulfur Substituted and a-Methylated Fatty Acids as Peroxisome Proliferator-Activated Receptor Activators,” Lipids (2005) 40:49-57. [cited by applicant]
Lilja-Hallberg, M. & Harrod, M., “Enzymatic Esterification of Long Polyunsaturated Fatty Acids and Lyso-Phosphatidylcholine in Isooctane and Ethanol,” Biocatalysis (1994) 9:195-207. [cited by applicant]
Livingston, J.R. & Drogin, R., “The Synthesis and Some Surface Active Properties of Alkylthioalkyl and Alkoxyalkyl Sulfates,” The Journal of the American Oil Chemists' Society (1965) 42:720-723. [cited by applicant]
Manallack DT et al., “The significance of acid/base properties in drug discovery,” [cited by applicant]
Masson, M. et al., “Marine Lipids for Prodrugs, Soft Compounds and Other Pharmaceutical Applications,” Pharmazie (2000) 55(3):172-177. [cited by applicant]
Matsumoto, M. et al., Orally Administered Eicosapentaenoic Acid Reduces and Stabilizes Atherosclerotic Lesions in ApoE-Deficient Mice, Atherosclerosis (2008) 197:524-533. [cited by applicant]
Meyer, K.L. et al., “In Vivo Evaluation of Phosphocholine and Quaternary Ammonium Containing Lipids as Novel Anti-HIV Agents,” J. Med. Chem. (1991) 34(4): 1377-1383. [cited by applicant]
Microcarrier Drug Delivery System, Huazhong University of Science and Technology Press, (ed. Cheng Fang), copyright 2009, pp. 217-219 (5 pages). [cited by applicant]
MIGLYOL® 812 and MIGLYOL® 810 product descriptions, http://www.petercremerna.com/products/159339301, accessed Jun. 4, 2019. (3 pages). [cited by applicant]
Müllertz A et al., “New perspectives on lipid and surfactant based drug delivery systems for oral delivery of poorly soluble drugs,” [cited by applicant]
Notice of Allowance in U.S. Appl. No. 12/741,890, issued Jan. 17, 2014. [cited by applicant]
Notice of Allowance in U.S. Appl. No. 13/054,212, issued Jan. 29, 2014. [cited by applicant]
Notice of Allowance in U.S. Appl. No. 13/319,101, issued Jan. 13, 2014. [cited by applicant]
Notice of Allowance in U.S. Appl. No. 13/883,405, issued Mar. 14, 2016. [cited by applicant]
Notice of Allowance in U.S. Appl. No. 14/770,086 issued Feb. 8, 2022. [cited by applicant]
Notice of Allowance in U.S. Appl. No. 14/770,086 issued Mar. 9, 2022. [cited by applicant]
Nystrom, R.F. & Brown, W.G., “Reduction of Organic Compounds by Lithium Aluminum Hydride. II. Carboxylic Acids,” Journal of the American Chemical Society (1947) 69(10):2548-2549. [cited by applicant]
Office Action (Restriction Requirement) for U.S. Appl. No. 13/574,132 dated Jan. 20, 2015. [cited by applicant]
Office Action dated Apr. 1, 2013, from U.S. Appl. No. 13/054,212. [cited by applicant]
Office Action dated Apr. 24, 2013, from U.S. Appl. No. 13/319,101. [cited by applicant]
Office Action dated Aug. 3, 2012, from U.S. Appl. No. 12/741,890. [cited by applicant]
Office Action dated Aug. 6, 2013, from U.S. Appl. No. 12/741,890. [cited by applicant]
Office Action dated Dec. 10, 2012, from U.S. Appl. No. 12/741,890. [cited by applicant]
Office Action dated Jan. 28, 2015, from U.S. Appl. No. 13/883,405. [cited by applicant]
Office Action dated Jan. 31, 2013, from U.S. Appl. No. 13/319,101. [cited by applicant]
Office Action dated Jul. 1, 2013, from U.S. Appl. No. 13/054,212. [cited by applicant]
Office Action dated Jul. 17, 2014, from U.S. Appl. No. 13/883,405. [cited by applicant]
Office Action for U.S. Appl. No. 14/263,793 dated Aug. 11, 2015. [cited by applicant]
Office Action from U.S. Appl. No. 13/319,101, dated Oct. 2, 2013. [cited by applicant]
Office Action (Restriction Requirement) from U.S. Appl. No. 14/770,862, dated Aug. 18, 2016. [cited by applicant]
Office Action from U.S. Appl. No. 14/770,862, dated Feb. 10, 2017. [cited by applicant]
Office Action from U.S. Appl. No. 14/770,862, dated Nov. 14, 2017. [cited by applicant]
Office Action from U.S. Appl. No. 14/770,862, dated Dec. 14, 2018. [cited by applicant]
Office Action from U.S. Appl. No. 14/770,862, dated Nov. 15, 2019. [cited by applicant]
Okoronkwo, A.E. et al., “Synthesis of w-Hydroxy-a-Alkyl/Aryl-y-Organo-Selenium and y-Organo-Tellurium: A New Class of Organochalcogen Compounds with Antinociceptive Activity,” Tetrahedron Letters (2008) 49:3252-3256. [cited by applicant]
Parkkari, T. et al., “a-Methylated Derivatives of 2-Arachidonoyl Glycerol: Synthesis, CB1 Receptor Activity, and Enzymatic Stability,” Bioorg. & Med. Chem. Lett. (2006) 16:2437-2440. [cited by applicant]
Patent Trial and Appeal Board Decision from U.S. Appl. No. 14/770,862 issued Oct. 18, 2021. [cited by applicant]
Pitt, M.J. et al., “Synthesis of Polyunsaturated is-Oxa Fatty Acids Via Rhodium Mediated Carbenoid Insertion,” Synthesis (1997) 7:1240-42. [cited by applicant]
Registry Copyright 2008 ACS on STN (RN 785712-42-7, 714185-72-5, 45247-37-8). [cited by applicant]
Ringbom, T. et al., “COX-2 Inhibitory Effects of Naturally Occurring and Modified Fatty Acids,” J. Nat. Prod. (2001) 64:745-749. [cited by applicant]
Rossmeisl, Martin et al., Prevention and Reversal o Obesity and Glucose Intolerance in Mice by DHA Derivatives, OBesity, vol. 17, No. 5, pp. 1023-1031 (2009). [cited by applicant]
Shchepin, R. et al., “Quorum Sensing in Candida albicans: Probing Farnesol's Mode of Action with 40 Natural and Synthetic Farnesol Analogs,” (2003) Chemistry & Biology 10:7 43-750. [cited by applicant]
Shirley, D.A. et al., “Alkylation with Long Chain p-Toluenesulfonates. IV. Alkylation of Alcohols and Amines with n-Octadecyl p-Toluenesulfonate,” Journal of Organic Chemistry (1953) 18:378-381. [cited by applicant]
Silverman, R.B., The Organic Chemistry of Drug Design and Drug Action, (Academic Press 1992), pp. 4, 14-28. [cited by applicant]
Silverman, R.B., The Organic Chemistry of Drug Design and Drug Action, 2nd Yes Edition, 19-20, (Chemical Industry Press, 2008) (Chinese). [cited by applicant]
Simopoulos, A.P., “Essential Fatty Acids in Health and Chronic Disease,” Am. J. Clin. Nutr. (1999) 70(Suppl):560S-569S. [cited by applicant]
Srisiri, W. et al., “Syntheses of Polymerizable Monoacylglycerols and 1,2-Diacylsn-Glycerols,” J. Org. Chem. (1996) 61 (16):5911-5915. [cited by applicant]
Stahl, P.H. & Wermuth, C.G., “Chapter 12: Monographs on Acids and Bases,” at 265-327, in “Handbook of Pharmaceutical Salts: Properties, Selection, and Use.” [cited by applicant]
Storlien, L.H. et al., “Polyunsaturated Fatty Acids, Membrane Function and Metabolic Diseases Such as Diabetes and Obesity,” Curr. Opin. Clin. Nutr. & Metab. Care (1998) 1 (6):559-563. [cited by applicant]
Supplementary European Search Report for European Patent Application No. 11 83 7647, dated Feb. 13, 2014. [cited by applicant]
Togashi, N. et al., “Antibacterial Activity of Long-Chain Fatty Alcohols Against Staphylococcus aureus,” Molecules (2007) 12: 139-148. [cited by applicant]
Tran, P.O.T. et al., “Inhibition of Interleukin-1 is-Induced COX-2 and EP3 Gene Expression by Sodium Salicylate Enhances Pancreatic Islet is-Cell Function,” Diabetes (2002) 51: 1772-78. [cited by applicant]
Tsotinis, A. et al., “Synthesis and Antiretroviral Evaluation of New Alkoxy and Aryloxy Phosphate Derivatives of 3′-Azido-3′ Deoxythymidine,” J. Med Chem (1996) 39:3418-3422. [cited by applicant]
Udding, J. et al., “Xanthate Transfer Cyclization of Glycolic Acid-Derived Radicals. Synthesis of Five-to Eight-Membered Ring Ethers,” J. Org. Chem. (1994) 59:6671-6682. [cited by applicant]
U.S. Appl. No. 62/84268 B1 filed by Awadhesh Mirshra, dated Sep. 2001. [cited by applicant]
Vaagenes, H. et al., “Methylated Eicosapentaenoic Acid and Tetradecylathioacetic Acid: Effects on Fatty Acid Metabolism,” Biochem. Pharmacol. (1999) 58:1133-1143._D. [cited by applicant]
Wang, P. et al., “Synthesis of Phospholipid-Inhibitor Conjugates by Enzymatic Transphosphatidylation with Phospholipase D,” J. Am. Chem. Soc. (1993) 115:10487-10491. [cited by applicant]
Weizmann, C. et al., “The Synthesis of a-Alkoxyisobutyric Acids and Alkyl Methacrylates from Acetonechloroform,” J. Am. Chem. Soc. (1948) 70:1153-1158. [cited by applicant]
Willumsen, N. et al., “Enhanced Hepatic Fatty Acid Oxidation and Upregulated Carnitine Palmitoyltransferase II Gene Expression by Methyl 3-Thiaoctadeca-6, 9, 12, 15-Tetraenoate in Rats,” J. Lipid Mediators Cell Signalin… [cited by applicant]
Willumsen, N. et al., “On the Effect of 2-Deuterium- and 2-Methyl-Eicosapentaenoic Acid Derivatives on Triglyerides, Peroxisomal is-Oxidation and Platelet Aggregation in Rats,” Biochimica et Biophysica Acta (1998) 1369:… [cited by applicant]
Woodbury, D.M. & Fingle, E., “Drugs Effective in the Therapy of the Epilepsies,” Basis of Therapeutics 201-26 (5th Ed. 1975). [cited by applicant]
Zeinalov, B.K., “Synthesis and Investigation of Esters of Alkyl Selenium Ethanols,” Azerbajdzanskij Chimiceskij Zurnal (1981) 5:41-43. [cited by applicant]