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- 2,926,180 United States Patent Office Patented Feb. 23, 1960 2 cycloalkyl, etc. These substituents R and R' may also be substituted with various groupings such as carboxyl 2,926,180 groups, sulfo groups, halogen atoms, etc. Examples of CONDENSATION OF AROMATIC KETONES WITH compounds which are included within the scope of this CARBOHYDRATES AND RELATED MATER ALS 5 general formula are acetophenone, propiophenone, benzo Carl B. Linn, Riverside, Ill., assignor, by mesne assign phenone, acetomesitylene, phenylglyoxal, benzylaceto ments, to Universal Oil Products Company, Des phenone, dypnone, dibenzoylmethane, benzopinacolone, Plaines, Ill., a corporation of Delaware dimethylaminobenzophenone, acetonaphthalene, benzoyl No Drawing. Application June 18, 1957 naphthalene, acetonaphthacene, benzoylnaphthacene, ben 10 zil, benzilacetophenone, ortho-hydroxyacetophenone, para Serial No. 666,489 hydroxyacetophenone, ortho - hydroxy-para - methoxy 5 Claims. (C. 260-345.9) acetophenone, para-hydroxy-meta-methoxyacetophenone, zingerone, etc. This application is a continuation-in-part of my co Carbohydrates which are condensed with aromatic pending application Serial No. 401,068, filed December 5 ketones to form a compound selected from the group 29, 1953, now Patent No. 2,798,079. consisting of an acylaryl-desoxy-alditol and an acylaryl This invention relates to a process for interacting aro desoxy-ketitol include simple sugars, their desoxy- and matic ketones with carbohydrates and materials closely omega-carboxy derivatives, compound sugars or oligo related to carbohydrates. The process relates more par saccharides, and polysaccharides. ticularly to the condensation of simple sugars, their 20 Simple sugars include dioses, trioses, tetroses, pentoses, desoxy- and their omega-carboxy derivatives, compound hexoses, heptoses, octoses, nonoses, and decoses. Com sugars or oligosaccharides, and polysaccharides with aro pound sugars include disaccharides, trisaccharides, and matic ketones in the presence of a hydrogen fluoride tetrasaccharides. Polysaccharides include polysaccharides catalyst. composed of only one type of sugar residue, polysac | An object of this invention is to produce organic 25 charides composed of more than one type of sugar unit, materials suitable for use per se or as intermediates in polysaccharides composed of one type of uronic acid the manufacture of detergents, pharmaceuticals, explo unit, i.e., polyuronides, polysaccharides composed of sives, gelling agents, surface coatings, resins, and oxida aldose (pentose or hexose) and uronic acid units, poly tion inhibitors by condensing aromatic ketones with saccharides containing hexose units esterified with an carbohydrates or with carbohydrate derivatives. 30 inorganic acid, and polysaccharides containing amino One embodiment of this invention relates to a process sugar units. which comprises condensing an aromatic ketone with a Utilizable simple sugars include the diose, glycolalde carbohydrate in the presence of a hydrogen fluoride hyde; trioses, such as glycerylaldehyde and s-dihydroxy catalyst to produce a compound selected from the group acetone; tetroses, such as erythrose, threose, erythrulose, consisting of an acylaryl-desoxy-alditol and an acylaryl 35 and apiose; the pentoses, such as arabinose, xylose, ribose, desoxy-ketitol, and recovering said resultant condensation lyxose, rhamnose (a methylpentose), fucose (a methyl product. pentose), rhodeose (a methylpentose), digitalose (a meth A specific embodiment of this invention relates to a oxymethylpentose), ketoxylose (a ketopentose), 2-desoxy process which comprises condensing acetophenone with ribose and 2-desoxy-methylpentose (digitoxose); hexoses, glucose in the presence of a hydrogen fluoride catalyst 40 such as mannose, glucose, idose, gulose, galactose, talose, to produce a 1-(acetophenyl)-1-desoxy-glucitol, and re allose, fructose, sorbose, tagatose, and psicose; heptoses, covering said resultant condensation product. such as glucoheptose, mannoheptose, galactoheptose, I have found that useful water-insoluble condensation Sedoheptose, mannoketoheptose, glucoheptulose, and products and also water-soluble condensation products perseulose; octoses, such as glucooctose, mannooctose, are formed by reacting aromatic ketones with carbo 45 and galactooctose; nonoses, such as glucononose, and hydrates and related substances in the presence of a mannononose; and decoses such as glucodecose. Desoxy hydrogen fluoride catalyst. These reactions may be car derivatives of simple sugars are formed by the replace ried out in steel equipment or other suitable apparatus ment of a hydroxyl substituent in a sugar with hydrogen lined with silver, copper, and certain alloys such as thereby forming a methyl or methylene linkage. The Monel metal and the like. This treatment may be ef 50 desoxypentoses and desoxyhexoses are the most com fected at temperatures of from about -40 C. to about monly occurring of such compounds. The omega-car 100. C. and preferably at temperatures of from about boxy derivatives of simple sugars, which are suitable in -10 C. to about --50 C. The pressure at which the the process of the present invention include tartronic reaction is carried out will vary with the reaction tem semialdehyde or its tautomer, hydroxypyruvic acid; perature used and the mol fractions of reactants and 55 alpha-gamma-dihydroxyacetoacetic acid, threuronic acid, hydrogen fluoride catalyst present. While many of the 4-keto-2,3,5-trihydroxypentanoic acid, xyluronic acid, condensation reactions are carried out at substantially 5-keto-tetrahydroxyhexanoic acids such as 5-keto-allonic atmospheric pressure, it may be desirable in certain in acid, 5-keto-gluconic acid, 5-keto-mannonic acid, 5-keto stances and with certain reactants to carry out the re gulonic acid, and 5-keto-galactonic acid; uronic acids action at pressures up to about 100 atmospheres or more. 60 containing 6 carbon atoms such as glucuronic acid, man It is convenient in most instances to operate the equip nuronic acid, and galacturonic acid, and the 6-keto-penta ment utilized at the pressure generated by the reaction hydroxyheptanoic acids. The simple sugars and their mixture and the catalyst contained therein. omega-carboxy derivatives, as starting materials for the Aromatic ketones which may be used as starting ma process of this invention, may be represented by the terials in the process of this invention may be represented 65 following general formula: by the following general formula: o 70 chor). in which R represents an aryl nucleus and R' is selected B - from the group consisting of alkyl, aryl, aralkyl, alkaryl, in which A equals H and CHOH, n equals an integer 3,926,180 3 4. from 1 to about 12 or so, and B equals H, CHOH, and and in some other instances it is most desirable to use COOH. As an example of the utility of this general anhydrous hydrogen fluoride as the catalyst. formula, when A=H, n=1, and B=H, the compound The process may be carried out by slowly adding a is glycolaldehyde; when A=H, n=1, and B=CHOH, hydrogen fluoride catalyst to a stirred mixture of aro the compound is glycerylaldehyde; when A=H, n=1, matic ketone and carbohydrate or related material being and B=COOH, the compound is tartronic semialdehyde, subjected to reaction while maintaining the reaction tem a tautomer of hydroxypyruvic acid; when A=CH2OH, perature at from about -40 to about 100° C. by suit n=1, and B=H, the compound is s-dihydroxyacetone; able cooling and/or heating means. It is often desirable when A=CH2OH, n=1, and B=CH2OH, the compound or advisable to commingle the reactants and catalyst at is erythrulose; when A=CHOH, na-1, and B-COOH, 0. relatively low temperatures such as from about -80 C. the compound is alpha-gamma-dihydroxyacetoacetic acid; to about -30 C. and then to permit the reaction mix when A=H, n=2, and B=CH2OH, the compound is ture to warm gradually while the reactants and catalyst - erythrose or threose; when A=H, n=2, and B-COOH, are stirred by suitable means such as a motor driven - the compound is threuronic acid; when A=CHOH, stirrer or other adequate mixing equipment. After the ins2, and B=CH2OH, the compound is riboketose or 5 reaction has reached the desired degree of completion, .xyloketose; when A=CHOH, n=2, and Bas-COOH, the the hydrogen fluoride catalyst is removed from the re compound is a 4-keto-2,3,5-trihydroxypentanoic acid; action mixture by distillation at atmospheric or lower ... when A=H, n=3, and B=CHOH, the compound is pressures, or by passing an inert gas through the reaction ribose, arabinose, xylose, or lyxose; when A=H, n=3, mixture while maintaining it at a relatively low tempera and B=COOH, the compound is a 5 carbon atom uronic 20 ture. Also the entire reaction mixture and catalyst may acid such as xyluronic acid; when A=CHOH, na-3, be mixed with water or may be added to ice in order and B2-CH2OH, the compound is psicose, fructose, to quench the activity of the hydrogen fluoride catalyst sorbose, or tagatose; when A=CHOH, n=3, and and to permit separation of the organic reaction products B-COOH, the compound is a 5-keto-tetrahydroxyhexa and unreacted starting materials from the catalyst. The noic acid; when A=H, n=4, and B=CHOH, the com 25 organic reaction products may also be separated from pound is allose, altrose, glucose, mannose, gulose, idose, aqueous hydrogen fluoride by means of an organic sol galactose, or talose; when A=H, n=4, and B-COOH, vent such as ether, in which some of the organic material the compound is a 6 carbon atom uronic acid such as may be dissolved. Further means of isolating the re glucuronic acid, mannuronic acid, and galacturonic acid; action products are illustrated in the examples. Thus 'when A=CH2OH, n=4, and B=CHOH, the compounds 30 the product formed by reacting acetophenone with glu are heptoses; and when A=CHOH, n=4, and B-COOH, cose or cellulose in the presence of substantially anhy - the compounds are 6-keto-pentahydroxyheptanoic acids. drous hydrogen fluoride at 30° C. separated into an ether The utilizable oligosacchrides or compound sugars Soluble and water-insoluble product and an ether-insolu : include disaccharides such as the pentose-hexose disac ble and water-soluble product.
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  • Patent No .: US 10703789 B2

    Patent No .: US 10703789 B2

    US010703789B2 ( 12 ) United States Patent ( 10 ) Patent No.: US 10,703,789 B2 De Fougerolles et al. (45 ) Date of Patent: * Jul. 7 , 2020 (54 ) MODIFIED POLYNUCLEOTIDES FOR THE (2013.01 ) ; A61K 38/36 ( 2013.01 ) ; A61K PRODUCTION OF SECRETED PROTEINS 38/363 ( 2013.01 ) ; A61K 38/44 ( 2013.01) ; A61K 38/4833 (2013.01 ) ; A61K 38/4846 ( 71 ) Applicant : Moderna TX , Inc., Cambridge, MA (2013.01 ) ; A61K 39/3955 ( 2013.01) ; A61K (US ) 47/10 (2013.01 ) ; A61K 47/54 (2017.08 ) ; A61K 47/542 (2017.08 ) ; A61K 48/0033 ( 2013.01 ) ; ( 72 ) Inventors: Antonin De Fougerolles, Waterloo A61K 48/0066 (2013.01 ) ; A61K 48/0075 ( BE ) ; Justin Guild , Framingham , MA (2013.01 ) ; CO7K 14/47 ( 2013.01 ) ; CO7K (US ) 14/475 ( 2013.01) ; CO7K 14/505 (2013.01 ) ; ( 73 ) Assignee : Moderna TX , Inc., Cambridge , MA CO7K 14/525 (2013.01 ) ; C07K 14/56 (US ) (2013.01 ) ; CO7K 14/565 ( 2013.01 ) ; CO7K 14/745 (2013.01 ) ; C07K 14/75 ( 2013.01) ; ( * ) Notice: Subject to any disclaimer , the term of this CO7K 16/2887 ( 2013.01 ) ; CO7K 16/32 patent is extended or adjusted under 35 ( 2013.01) ; CO7K 19/00 ( 2013.01) ; C12N U.S.C. 154 (b ) by 0 days . 9/0069 ( 2013.01) ; C12N 9/644 ( 2013.01 ) ; C12N 15/85 (2013.01 ) ; C12N 15/88 This patent is subject to a terminal dis ( 2013.01 ) ; C12Y 113/12007 (2013.01 ) ; C12Y claimer . 304/21005 (2013.01 ) ; C12Y 304/21022 (2013.01 ) ; A61K 9/0019 (2013.01 ) ; A61K (21 ) Appl. No.: 16 /438,978 48/00 (2013.01 ) ; C12N 2840/00 (2013.01 ) ( 22 ) Filed : Jun .