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Atoa Wa Ni Mha La Maison ATOAUS009975847B2 WA NI MHA LA MAISON (12 ) United States Patent ( 10 ) Patent No. : US 9 ,975 , 847 B2 Gambogi et al. (45 ) Date of Patent: May 22 , 2018 ( 54 ) AMINO ACID DERIVATIVES AND THEIR 2006 /0013778 A1 1 / 2006 Hodosh 2008/ 0317839 Al * 12/ 2008 Quay .. .. .. .. .. A61K 9 / 1272 USES 424 / 450 ( 71) Applicant: Johnson & Johnson Consumer Inc ., 2010 /0330136 Al 12 /2010 Rocabayera Bonvila Skillman , NJ (US ) FOREIGN PATENT DOCUMENTS (72 ) Inventors : Robert J . Gambogi, Hillsborough , NJ JP 5982310 5 / 1984 (US ) ; Anthony R . Geonnotti, III , WO WO2000 /011022 2 / 2000 Princeton , NJ (US ) ; Michael C . Giano , WO WO2003 /013454 2 / 2003 Southampton , NJ ( US ) ; Latrisha WO WO 2005 /000261 AL 1 /2005 Petersen , Highland Park , NJ (US ) WO WO2008 / 137758 A2 11/ 2008 (73 ) Assignee : Johnson & Johnson Consumer Inc . , OTHER PUBLICATIONS Skillman , NJ (US ) Kazuhiko et al . JPS 5982310 ( A ) ( 1984 ) English Abstracts . * Pinazo , A . ; New cationic vesicles prepared with double chain ( * ) Notice : Subject to any disclaimer , the term of this surfactants fromarginine: Role of the hydrophobic group on the patent is extended or adjusted under 35 antimicrobial activityand cytotoxicity ; Colloids and Surfaces B : U . S . C . 154 (b ) by 15 days. Biointerfaces 141 ( 2016 ) 19 - 27 . International Search Report dated Jan . 21, 2016 ; — Int' l Appln . No. ( 21) Appl . No. : 14 /938 , 334 PCT/ US2015 / 060166 filed Nov . 11, 2015 . Morrison and Boyd , Organic Chemistry Fourth Edition , section ( 22 ) Filed : Nov . 11 , 2015 20 . 3 , p . 814 . Yang Xu and R . F . Pratt , “ -Lactam -Recognizing Enzymes Exhibit (65 ) Prior Publication Data Different Structural Specificity in Acyclic Amide and Ester Sub strates : A Starting point in B -Lactamase Evolution ? ” Bioorganic & US 2016 /0145203 A1 May 26 , 2016 Medicinal Chemistry Letters, vol . 4 . No . 19 . pp . 2291 - 2296 ( 1994 ) . Zhaozhao Li, et al . “ Peptide a -Keto Ester, a -Keto Amide, and a - Keto Acid Inhibitors of Calpains and Other Cysteine Proteases ” J . Related U . S . Application Data Med . Chem . 1993 , 36 , 3472 - 3480 . ( 60 ) Provisional application No . 62 / 078 , 187 , filed on Nov . 11 , 2014 * cited by examiner (51 ) Int . Ci. Primary Examiner — Mark V Stevens C07C 279 / 12 ( 2006 .01 ) (57 ) ABSTRACT A61K 8 /43 ( 2006 . 01 ) Provided are compounds described by the Formula I : A610 11 / 00 ( 2006 .01 ) A61K 8 /44 ( 2006 .01 ) C07C 237 / 22 ( 2006 .01 ) (52 ) U . S . CI. av ??? . C07C 279 / 12 ( 2013 . 01 ) ; A61K 8 /43 ( 2013 .01 ) ; A61K 8 /44 (2013 .01 ) ; A61Q 11/ 00 ( 2013 .01 ) ; C07C 237 /22 (2013 .01 ) N ( 58 ) Field of Classification Search CPC . A61K 8 / 43; A61K 8 / 44 ; A61Q 11 /00 ; C07C 237 /22 ; C07C 279 / 12 wherein : R is a linear or branched , saturated or unsaturated See application file for complete search history . aliphatic group having from 5 to 22 carbon atoms; R , is (56 ) References Cited selected from the group consisting of the functional groups : U . S . PATENT DOCUMENTS NH 4 ,051 , 234 A 9 / 1977 Gieske et al . – NH2; 4 , 994 , 262 A 2 / 1991 Charbonneau et al. NH 5 , 190 ,747 A 3 / 1993 Sekiguchi et al. 5 , 328 ,682 A 7 / 1994 Pullen et al. H2N 5 , 874 , 068 A 2 / 1999 Engelman et al. 6 , 121, 315 A 9 / 2000 Nair et al. 6 , 416 , 745 B1 7 / 2002 Markowitz et al. and salts thereof; n is from 0 to 4 ; and Rz is a linear or 6 , 682 , 722 B2 1 / 2004 Majeti et al. branched , saturated or unsaturated aliphatic group having 7 , 084 , 104 B2 8 /2006 Martin et al . from 1 to 6 carbon atoms. Also provided are compositions 7 , 087 ,650 B2 8 / 2006 Lennon comprising , and methods of use of, the compounds of the 7 , 417 , 020 B28 / 2008 Fevola et al . 2005 / 0027001 A1 * 2 / 2005 Boyd A61Q 11/ 00 present invention . 514 /551 20 Claims, 3 Drawing Sheets U . S . Patent May 22, 2018 Sheet 1 of 3 US 9 , 975 , 847 B2 801. 5 ULUUL zju oldi. 376997. 591 www Max:1.26821e+006 008 ?worden www.mamalinnanlanmiwa 020 8 ROur0914 .7 508. 13 009 ?8 * s # ????84488????? & & 009 * & w ooowwwww 4????8???8????????? *MSD1SPC,time-3.162:284ofC\EZXDATAchemisELAWSONMGLAEA1200227280514D+BSBESAPIPosScanFragVar NA 109 444. 2 VIV 009 LACAO wdro SUV-V 821 .1 4 . 385 $ 007007 ¥ DAD1A,Sig=2204Ref-360100(ELAWSONMGLAEA1200227280514.DO minimumananthanandhamini 20.3 bobanknotwikkeleitamabahkatakkahluukeskustelutubandukthandada 008008 Der wwwwwwwwwwwww miniumininim Woooong000000w.w 522. 40 ???????????????????????????????????????????????.??????????? ZOZOTE 007007 10 llllllllllllllllllllllllllllllllll MAU:3003 100withinh musikenlembusataminstrumentenkwekenntundentenkninska wiiniintinin U . S . Patent May 22, 2018 Sheet 2 of 3 US 9 , 975 , 847 B2 , 800* Max:169069 - groep 700 wer . wwwpo . 600 . ghe . n . *400500600760 . 500 n . e FIG.2 *MSD1SPC,time=0.269:659ofC\EZ/DATAchemisELAWSON-MGLAEA1100226280514DESAPIPosScanFragVar i 5 .387 5. 388 d wwwpropexwwxxxmorgongewape 400 5. 385 - 5. 384 3052 - 300 2613 - *200300 217 200 . Lamanini 7-100 Vppers CO. p ocopank TESXoooooooooooooooo ZAKAYA KKKK A RDOOR U . S . Patent May 22, 2018 Sheet 3 of 3 US 9 ,975 ,847 B2 Shell typromptonphotography 1.890089649916163013003.728401 reper 84301.123 ChemicalShift(ppm) FIG.3 7.06543302520151 94.0 Internet better fil 0.15 Intensity Normalized ?????????????????????????????????????????????????????????????????????????????????????? US 9 ,975 ,847 B2 AMINO ACID DERIVATIVES AND THEIR ethandisulfonate , fumarate , gluconate , hippurate , USES iodide , fluoride , lactate , laurylsulfate , malate , laeate , mesylate , methysulfate , napsylate , nitrate , octadecano CROSS REFERENCE TO RELATED ate , oxalate , pamoate , phosphate , polygalacturonate , APPLICATION 55 succinate , sulfate , tartrate , and tosylate ; n is from 0 to 4 ; and This application claims the benefit of U . S . Provisional Rz is a linear or branched , saturated or unsaturated ali Application Ser. No . 62/ 078 , 187 , filed Nov. 11 , 2014 . phatic group having from 1 to 6 carbon atoms. The compositions of Formula I may have any suitable BACKGROUND 10 linear or branched , saturated or unsaturated aliphatic group having from 5 to 22 carbons for R . Examples of suitable A variety of amino acid derivatives are known in the art linear or branched , saturated or unsaturated aliphatic groups for a variety of uses . For example , U . S . Pat . No . 5 ,874 , 068 , having from 5 to 22 carbons include, C to C22 linear or WO02003 /013454 , and US2010 /0330136 disclose the use of branched alkyl groups, such as , pentyl, hexyl, heptyl, octyl, Lauryl arginine ethyl ester (“ LAE ” ) , and certain related 15 nonyl, decyl , undecyl, dodecyl , up to docosanyl , and the compounds, for use in oral compositions. In addition , LAE like ; as well as, C , to C2, linear or branched alkylene groups is currently used in hydroalcoholic mouth rinses to prevent such as myristolyl up to docasanhexayl, and the like. bacterial attachment. However, applicants have recognized In certain embodiments , R , is linear or branched alkyl that LAE tends to lack sufficient stability to be useful in group having a carbon chain of from 5 to 22 carbons atoms, low - alcohol or alcohol- free mouth rinses . 20 including for example, pentyl, hexyl, heptyl, octyl , nonyl, In addition , other documents such as WO2008 /137758A2 decyl , undecyl, dodecyl up to docasonyl. In certain other and WO2000 /011022 disclose broad classes of compounds, embodiments , R is linear or branched alkyl group having a which may include certain amino acid derivatives , for uses carbon chain of from 7 to 18 carbons atoms, including for such as for drug delivery or anti -tumor end benefits , respec example , heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tively . 25 tridecyl, tetradecyl , pentadecyl, hexadecyl, heptadecyl and octadecyl. In still other embodiments , Ry is linear or BRIEF DESCRIPTION OF THE DRAWINGS branched alkyl group having a carbon chain of from 9 to 14 carbons atoms, including for example , decyl, undecyl, dode FIG . 1 is an HPLC chromatograph and a mass spectrom cyl up to tetradecyl. In certain embodiments, R , is an etry graph of [ amino ( { [ 4 -dodecanamido - 4 - ( ethylcarbamoyl ) 30 undecyl group . In certain embodiments , R , is a heptyl group . butyl] amino } )methylidene ] azanium . In certain embodiments , R , is a heptadecyl group . FIG . 2 is a drawing of the chemical structure and mass In certain embodiments , R , is linear or branched alkenyl spectrometry graph of famino ( { [ 4 -dodecanamido - 4 - ( ethyl- group having a carbon chain of from 5 to 22 carbons atoms, carbamoyl) butyl ] amino } )methylidene ] azanium . including for example , 9 -hexadecenyl , 9 -octadecenyl , FIG . 3 : is a ' H - NMR graph of [ amino ( { [ 4 -dodecanamido - 35 11 -decenyl , 9 , 12 -octadecandienyl , 9 , 12 , 15 -octadecatrienyl , 4 - ( ethylcarbamoyl ) butyl ] amino } )methylidenejazanium . 6 , 9 , 12 -octadecatrienyl , 9 - eicosenyl, 5 , 8 , 11, 14 - eicosatetra enyl, 13 -docosenyl and 4 , 7 , 10 , 13, 16 , 19 - docosaheaenyl. In DESCRIPTION OF THE INVENTION certain other embodiments , R , is linear or branched alkenyl group having a carbon chain of from 16 to 20 carbons atoms, The present invention relates to new amino acid deriva - 40 including for example , 9 -hexadecenyl , 9 - octadecenyl , tives developed by applicants that are described by the 11- decenyl, 9 , 12 -octadecandienyl , 9 , 12 ,15 -octadecatrienyl , Formula 1 : and 6 , 9 , 12 - octadecatrienyl. In certain embodiments , R , is a branched alkyl group having a carbon chain of from 5 to 22 carbons atoms, ( 1) 45 including for example
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