( 12 ) United States Patent

( 12 ) United States Patent

US009861611B2 (12 ) United States Patent ( 10 ) Patent No. : US 9 ,861 , 611 B2 Bromley ( 45 ) Date of Patent: * Jan . 9 , 2018 (54 ) FORMULATIONS OF WATER -SOLUBLE 2 ,703 , 047 A 3 / 1955 Pauli et al . .. .. 101 / 8 DERIVATIVES OF VITAMIN E AND SOFT 3 , 102 ,078 A 8 / 1963 Robeson et al . .. .. 514 /458 3 , 124 , 840 A 3 / 1964 Taylor . .. .. 425 / 122 GEL COMPOSITIONS , CONCENTRATES 3 , 203 , 347 A 8 / 1965 Llyod et al. 101/ 219 AND POWDERS CONTAINING SAME 3 , 333 ,031 A 7 / 1967 Chue et al. 264 / 15 3 ,480 ,616 A 11/ 1969 Osipow et al. .. .. .. .. 536 / 119 ( 71 ) Applicant: VIRUN , INC ., Walnut, CA (US ) 3 , 538 , 119 A 11 / 1970 Grant . .. .. 549 /410 3 ,644 , 333 A 2 / 1972 Osipow et al . .. .. .. .. 536 / 119 3 ,714 , 144 A 1 / 1973 Feuge et al . 536 / 119 (72 ) Inventor : Philip J . Bromley , Fullerton , CA (US ) 3 ,917 , 859 A 11/ 1975 Terada et al . 426 /602 4 , 353 , 365 A 10 / 1982 Hallworth et al. .. .. 128 / 203 . 15 ( 73 ) Assignee : Virun, Inc. , Pomona , CA (US ) 4 ,524 ,769 A 6 / 1985 Wetterlin et al . .. 128 /203 . 15 4 , 572 ,915 A 2 / 1986 Crooks . .. .. .. 514 /458 ( * ) Notice: Subject to any disclaimer, the term of this 4 , 665 ,204 A 5 / 1987 Wirth .. 549 /410 patent is extended or adjusted under 35 4 ,670 , 285 A 6 / 1987 Clandinin et al. .. .. 426 /602 4 ,710 , 567 A 12 / 1987 Kea et al . .. 536 / 119 U . S . C . 154 ( b ) by 0 days. 4 , 780 , 316 A 10 / 1988 Brox . 424 / 456 This patent is subject to a terminal dis 4 , 835 ,002 A 5 / 1989 Wolf et al . .. .. .. .. 426 / 590 4 , 867 , 986 A 9 / 1989 Desai et al. .. 424 / 464 claimer . 4 , 898 , 935 A 2 / 1990 Nakamura et al . .. 536 / 119 4 , 995 , 911 A 2 / 1991 Matsumoto et al . .. .. 127 /48 (21 ) Appl. No. : 14 / 866 ,808 4 , 996 , 309 A 2 / 1991 Matsumoto et al . 536 / 119 5 ,011 ,922 A 4 / 1991 Matsumoto et al . .. .. 536 / 119 ( 22 ) Filed : Sep . 25 , 2015 5 , 017 ,697 A 5 / 1991 Matsumoto et al . .. 536 / 127 5 , 035 , 237 A 7 / 1991 Newell et al. .. .. 128 / 203. 15 5 , 179 , 122 A 1 / 1993 Greene et al . .. .. .. .. .. 514 /458 (65 ) Prior Publication Data 5 , 234 ,695 A 8 / 1993 Hobbs et al . .. .. .. .. .. .. .. 424 /489 US 2016 /0081976 A1 Mar . 24 , 2016 (Continued ) Related U . S . Application Data FOREIGN PATENT DOCUMENTS (63 ) Continuation of application No . WO WO 95 /31217 11/ 1995 PCT/ US2015 / 051097 , filed on Sep . 18 , 2015 , and a WO 96 / 36316 11 / 1996 continuation of application No . (Continued ) PCT/ US2015 /051083 , filed on Sep . 18 , 2015 . (60 ) Provisional application No. 62/ 052, 433 , filed on Sep . OTHER PUBLICATIONS 18 , 2014 , provisional application No . 62 /052 ,450 , Letter /Written Disclosure of the Supplemental Information Disclo filed on Sep . 18 , 2014 , provisional application No . sure Statement for the above - reference application , filed herewith 62/ 052 ,435 , filed on Sep . 18 , 2014 . on Dec . 18 , 2015 , 2 pages. Bromley , P . J ., “ Nanotechnology and Nonpolar Active Compounds (51 ) Int. Cl. in Functional Foods: An Application Note , ” Bio -Nanotechnology : A A61K 31/ 355 ( 2006 . 01 ) Revolution in Food , Biomedical and Health Sciences ( eds D . A61K 31/ 09 ( 2006 .01 ) Bagchi, M . Bagchi, H . Moriyama and F . Shahidi) , Blackwell A61K 31/ 202 ( 2006 .01 ) Publishing Ltd . , Oxford , UK , pp . 697 -703 ( 2013 ) . A61K 31/ 437 ( 2006 . 01) Brouwers et al. “ Intraluminal drug and formulation behavior and A61K 31/ 122 ( 2006 .01 ) integration in in vitro permeability estimation : a case study with A61K 36 / 324 ( 2006 .01 ) amprenavir. ” J. Pharm . Sci . 95 :372 - 383 (2006 ) . A61K 45 /06 ( 2006 .01 ) (Continued ) A61K 36 /82 ( 2006 .01 ) (52 ) U . S . CI. CPC . .. .. .. .. .. A61K 31 /355 ( 2013 .01 ) ; A61K 31 /09 Primary Examiner - Mark V Stevens (2013 .01 ) ; A61K 31/ 122 ( 2013 .01 ) ; A61K ( 74 ) Attorney , Agent, or Firm — Dentons US LLP ; 31 /202 (2013 . 01 ) ; A61K 31/ 437 (2013 .01 ) ; Stephanie Seidman A61K 36 /324 (2013 .01 ) ; A61K 36 / 82 (2013 .01 ) ; A61K 45 /06 ( 2013 .01 ) ( 58 ) Field of Classification Search (57 ) ABSTRACT CPC .. .. .. A61K 31 /475 ; A61K 47 / 22 , A61K 47 /36 ; Provided herein are compositions that contain water - soluble A61K 9 / 107 ; A61K 9 / 1617 ; A23L 33 / 10 : vitamin E derivative mixtures ( compositions ) , such as A23L 33 / 12 , A23L 33 / 15 ; A23P 10 / 40 tocopheryl polyethylene glycol succinate ( TPGS ), TPGS See application file for complete search history . analogs, TPGS homologs and TPGS derivatives . The water soluble vitamin E mixtures contain mixtures of dimers and (56 ) References Cited monomers of the vitamin E derivative . Provided are prod ucts containing the water- soluble vitamin E derivative mix U . S . PATENT DOCUMENTS tures , including capsules , soft gel compositions , pre - gel 2 , 449 , 139 A 9 / 1948 Posner .. .. .. .. .. .. .. .. 425 / 5 compositions, emulsions and powders . 2 ,623 ,494 A 12 / 1952 Pauli . .. .. 118 / 704 2 ,680 ,749 A 6 / 1954 Cawley et al. .. .. .. 549 /410 2 ,688 ,775 A 9 / 1954 Pauli et al. .. .. .. .. .. .. 264 / 293 31 Claims, No Drawings US 9 , 861, 611 B2 Page 2 (56 ) References Cited 2005 /0163828 A1 7 / 2005 Bernard et al. .. .. .. 525 /411 2005 / 0208082 A1 9 / 2005 Papas et al. .. .. .. .. 424 / 400 U . S . 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