Patented Jan. 1, 1924.
`
`1,479,293
`
`UNITED STATES PATENT OFFICE.
`
`MARTIN FREUND, DECEASED, LATE OF FRANKFORT-ON-THE-MAIN, GERMANY; :BY
`WALTER FREUND, ADMINISTRATOR, OF FRANKFORT-ON-THE-MAIN, AND EDMUND
`SPEYER, OF FRANKFORT-ON-THE-MAIN, GERMANY.
`
`PRODUCT OF REDUCTION OF OXYCODEINON AND PROCESS OF PREPARING THE SAME,
`
`N'o Drawing. Original application filed July 15, 1921, Serial No. 485,130. Divided and this application
`filed March 15, 1922. Serial No. 544,010.
`
`oo
`
`(GRANTED UNDER THE PROVISIONS OF THE ACT OF MARCH 3, 1921, 41 STAT. L., 1313.)
`To all1.o hom it may concern:
`cvlumns melting at 268 to 270° G. Its free 60
`Be it known that MARTIN FREuND, de-
`base is precipitated from solutions of the
`ceased~ formerly a resident of Frankfort-
`salts by ammonia, soda or alkalies; it is in-
`on-the-Main, for whom the undersigned
`soluble in excess of alkalies. It combines
`with methyl iodide to form C18H 21N0 4.CH3I
`5 WALTER FREUND, residing at Frankfort-on-
`the-Main, Germany, citizen of the German
`a compound representing prisms which de- 55
`Republic, is acting administrator, and I,
`compose at 251 o C. Its ketone character is
`EDliiUND SPEYF£, a resident of Frankfort-
`shown by the formativn of an oxime, the
`hydrochloride of which: C18H 22N p 4.HCl is
`on-the-Main, Germany, a citizen of the Ger-
`lO man Republic, have invented certain new
`isolated in small sticks decomposing at 275
`and useful Improvements in a Product of
`to 278° C.
`Reduction of Oxycodeinon and Processes of
`The new dihydrooxycodeinon is to be used
`Preparing the Same (for which we have made
`in medicine ancl pharmacy.
`application in Germany April14, 1916, Pat-
`Example: 10 grms. oxycodeinon are heat-
`Hi ent No. 296,916; in Austria Dec. 9, 1916,
`ed with a solution of 20 grms. oodium
`Patent No. 75,740; in Hungary Dec. 9, 1916,
`hydrosulphite· Na2S 20 4
`in 60 cc. water. 175
`Patent No. 71,587; in Switzerland Dec. 7,
`After a short time complete solution takes
`1916, Patent No. 75,110; in Norway Dec. 30,
`place. Upon supersaturating with soda or
`1919, Patent No. 31,350; in Czechoslovakia
`ammonia 6 grams dihydrooxycvdeinon are
`separated in crystalline form.
`20 Feb. 10, 1920, Patent No. 2228; in Denmark
`Dec. 29, 1919; in Sweden Jan. 20, 1920; in
`Having thus described this invention, we
`Italy Feb. 23, 1920, and Netherlands Dec.
`claim as new and desire to secure by Let- 70
`ters Patent:
`·
`31, 1919), of which the following is a clear,
`full, and exact description.
`1. The process v:f preparing dihydrooxy-
`The subject of this invention is dihydro-
`codeinon, melting at 222° C., which consists
`in boiling oxycodeinon together with a solu-
`oxycocleinon, an unknown derivative of oxy-
`tion of sodium hydrosulphite.
`codeinon-a product described in the Ger-
`man Letters Patent No. 286431-and the
`2. A new product of reduction, obtained
`process of preparing the same.
`by heating oxycodeinvn together with a
`Oxycodeinon,
`having
`the
`formula
`solution of sodium hydrosulphite, dihydro-
`oxycodeinon having the formula C18H 21N04 ,
`C18H 19N04 and a melting point of 275° C.,
`which crystallizes from alcohol in long 80
`by boiling with a solution of sodium hydro-
`sulphite, is reduced to dihydrooxycodeinon
`jagged columns, melting at 222° C., and
`yields well crystallized salts and forms an
`of the formula C18H 21N04 • Dihydrooxy-
`:J3 cocleinon prepared in such manner is ac-
`oxime, the hydrochloride of which is iso-
`tually identical with dihydrooxycocleinon as
`lated in small sticks decomposing at 275 to
`278° C.
`prepared in accordance with the specifica-
`tion of the patent application Serial Number
`In testimony whereof we have hereunto
`signed our names in the presence of the two
`485130, filed July 15, 1921, from which this
`subscribing witnesses.
`40 application is a divisional application.
`DR. WALTER FREUND,
`The identity is shown by the following
`Acting administrator upon the estate of the
`:facts. Dihydrooxycodeinon prepared in ac-
`deceased inventor, Martin Freund.
`cordance with this application crystallizes
`PRIVATE AGENT DR. EDMUND SPEYER.
`from alcohol in long jagged columns melt-
`45 ing at 222° C. and yields well crystallized
`Witnesses:
`Its hydrochloride C18H 20N04.HCl
`FRITZ MAYER,
`salts.
`FRIEDRICH L. HAHN.
`crystallizes from water or diluted alcohol in
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`25
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`30
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`75
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`85
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`KASHIV1002
`IPR of Patent No. 9,492,392
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`