<?xml version="1.0" encoding="ISO-8859-1"?><article xmlns:mml="http://www.w3.org/1998/Math/MathML" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance">
<front>
<journal-meta>
<journal-id>0138-6557</journal-id>
<journal-title><![CDATA[Revista Cubana de Medicina Militar]]></journal-title>
<abbrev-journal-title><![CDATA[Rev Cub Med Mil]]></abbrev-journal-title>
<issn>0138-6557</issn>
<publisher>
<publisher-name><![CDATA[Centro Nacional de Información de Ciencias MédicasEditorial Ciencias Médicas]]></publisher-name>
</publisher>
</journal-meta>
<article-meta>
<article-id>S0138-65572020000300012</article-id>
<title-group>
<article-title xml:lang="es"><![CDATA[Método modificado para la síntesis de hidrocloruro de amantadina]]></article-title>
<article-title xml:lang="en"><![CDATA[A modified method for synthesis of amantadine hydrochloride]]></article-title>
</title-group>
<contrib-group>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Binh Vu]]></surname>
<given-names><![CDATA[Duong]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Huy Le]]></surname>
<given-names><![CDATA[Binh]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Hong Bui]]></surname>
<given-names><![CDATA[Thi]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Duc Do]]></surname>
<given-names><![CDATA[Anh]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Dinh Phan]]></surname>
<given-names><![CDATA[Chau]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Do]]></surname>
<given-names><![CDATA[Quyet]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
</contrib-group>
<aff id="Af1">
<institution><![CDATA[,Vietnam Military Medical University  ]]></institution>
<addr-line><![CDATA[Hanoi ]]></addr-line>
<country>Vietnam</country>
</aff>
<aff id="Af2">
<institution><![CDATA[,The R&amp;D department, 3B6 chemical service and production joint-stock company  ]]></institution>
<addr-line><![CDATA[Hanoi ]]></addr-line>
<country>Vietnam</country>
</aff>
<aff id="Af3">
<institution><![CDATA[,Hanoi University of Science and Technology School of Chemical Engineering ]]></institution>
<addr-line><![CDATA[Hanoi ]]></addr-line>
<country>Vietnam</country>
</aff>
<aff id="Af4">
<institution><![CDATA[,Universidad de Ciencias Médicas de las Fuerzas Armadas Revolucionarias  ]]></institution>
<addr-line><![CDATA[La Habana ]]></addr-line>
<country>Cuba</country>
</aff>
<pub-date pub-type="pub">
<day>00</day>
<month>09</month>
<year>2020</year>
</pub-date>
<pub-date pub-type="epub">
<day>00</day>
<month>09</month>
<year>2020</year>
</pub-date>
<volume>49</volume>
<numero>3</numero>
<copyright-statement/>
<copyright-year/>
<self-uri xlink:href="http://scielo.sld.cu/scielo.php?script=sci_arttext&amp;pid=S0138-65572020000300012&amp;lng=en&amp;nrm=iso"></self-uri><self-uri xlink:href="http://scielo.sld.cu/scielo.php?script=sci_abstract&amp;pid=S0138-65572020000300012&amp;lng=en&amp;nrm=iso"></self-uri><self-uri xlink:href="http://scielo.sld.cu/scielo.php?script=sci_pdf&amp;pid=S0138-65572020000300012&amp;lng=en&amp;nrm=iso"></self-uri><abstract abstract-type="short" xml:lang="es"><p><![CDATA[RESUMEN  Introducción:  El hidrocloruro de amantadina (I) es conocido como un medicamento antiviral utilizado para prevenir y tratar las infecciones por influenza A. También se utiliza para aliviar los síntomas de la enfermedad de Parkinson en el período inicial. Se han informado varios métodos para la preparación de (I). Estos procedimientos comienzan con adamantano (II) en cuatro o tres pasos de reacción, para producir hidrocloruro de amantadina con rendimientos globales que van del 45 % al 58 %.  Objetivo:  Mejorar el método para la síntesis de hidrocloruro de amantadina, que puede introducirse a escala industrial.  Métodos:  La optimización paso a paso para reducir el uso de reactivos, disolventes, así como las condiciones de cada paso, se seleccionaron para ser menos agresivas y más amigables con el medio ambiente.  Resultados:  Todos los factores relacionados con el rendimiento de la reacción para sintetizar los compuestos intermedios y finales se seleccionaron para obtener el mayor rendimiento de cada etapa. Finalmente, se estableció un procedimiento de dos pasos para la síntesis de (I) a partir de (II), a través de N- (1-adamantil) formamida (III), con un rendimiento global mejorado del 78 % y una pureza del 99,2 %. Se confirmó la estructura del producto por 1H-NMR, 13C-NMR, IR y MS. La síntesis de N- (1-adamantil) formamida (VI) a partir de (II) también se logró con éxito en un solo paso. Este método evita el uso de bromo líquido o ácido sulfúrico gaseoso como reactivos. La conversión posterior de (VI) a (I) se llevó a cabo bajo condiciones de reacción, más suaves sin usar solventes peligrosos.  Conclusiones:  Se logró la síntesis mejorada del clorhidrato de amantadina (I). Este resultado puede utilizarse en una producción industrialmente conveniente. Las materias primas y reactivos utilizados en esta investigación son baratas y están disponibles. El tiempo total de preparación se redujo significativamente, con ahorro de energía y mano de obra.]]></p></abstract>
<abstract abstract-type="short" xml:lang="en"><p><![CDATA[ABSTRACT  Introduction:  Amantadine hydrochloride (I) was well-known as an antiviral drug used to prevent and treat influenza A infections. Besides, it also was used to relieve the symptoms of Parkinson's disease in the early period. Several methods for the preparation of I have been reported. These procedures started with adamantane (II) in four or three reaction steps to produce amantadine hydrochloride with overall yields ranging from 45% to 58%.  Objectives:  Improving method for synthesis of amantadine hydrochloride could introduce to industrial scale.  Methods:  Step-by-step optimization to reduce the use of reagents, solvents, as well as the conditions of each step were screened to be milder and more environment-friendly.  Results:  All factors related to the yield of reaction to synthesize the intermediate and final compounds were screened to give the highest yield of each step. Finally, a two-step procedure for the synthesis of (I) from (II) via N-(1-adamantyl) formamide (III) with improving overall yield of 78% and a purity of 99.2% was established, and the structure of the product was confirmed by 1H-NMR,13C-NMR, IR and MS. The synthesis of N-(1-adamantyl) formamide (VI) from (II) also was successfully accomplished within only one step. This method avoided the use of liquid bromine or fuming sulfuric acid as reactants. The subsequent conversion of (VI) to (I) was carried out under milder reaction conditions without using hazardous solvents.  Conclusions:  An improved synthesis for amantadine hydrochloride (I) have been provided. This research can be an industrially convenient production of amantadine hydrochloride. Because the raw materials and reagents used in this research are cheap and available which also were screened to save their use. Moreover, the total preparation time was significantly reduced to save energy as well as labor.]]></p></abstract>
<kwd-group>
<kwd lng="es"><![CDATA[clorhidrato de amantadina]]></kwd>
<kwd lng="es"><![CDATA[adamantino]]></kwd>
<kwd lng="es"><![CDATA[N- (1-adamantil) acetamida]]></kwd>
<kwd lng="es"><![CDATA[antivírico]]></kwd>
<kwd lng="es"><![CDATA[antidisquinético]]></kwd>
<kwd lng="en"><![CDATA[amantadine hydrochloride]]></kwd>
<kwd lng="en"><![CDATA[adamantine]]></kwd>
<kwd lng="en"><![CDATA[N-(1-adamantyl) acetamide]]></kwd>
<kwd lng="en"><![CDATA[antiviral]]></kwd>
<kwd lng="en"><![CDATA[antidyskinetic]]></kwd>
</kwd-group>
</article-meta>
</front><back>
<ref-list>
<ref id="B1">
<label>1</label><nlm-citation citation-type="journal">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Davies]]></surname>
<given-names><![CDATA[WL]]></given-names>
</name>
<name>
<surname><![CDATA[Grunert]]></surname>
<given-names><![CDATA[RR]]></given-names>
</name>
<name>
<surname><![CDATA[Haff]]></surname>
<given-names><![CDATA[RF]]></given-names>
</name>
<name>
<surname><![CDATA[McGahen]]></surname>
<given-names><![CDATA[JW]]></given-names>
</name>
<name>
<surname><![CDATA[Neumayer]]></surname>
<given-names><![CDATA[EM]]></given-names>
</name>
<name>
<surname><![CDATA[Paulshock]]></surname>
<given-names><![CDATA[M]]></given-names>
</name>
</person-group>
<article-title xml:lang=""><![CDATA[Antiviral Activity of 1-Adamantanamine (Amantadine)]]></article-title>
<source><![CDATA[Science]]></source>
<year>1964</year>
<volume>144</volume>
<numero>3620</numero>
<issue>3620</issue>
<page-range>862-3</page-range></nlm-citation>
</ref>
<ref id="B2">
<label>2</label><nlm-citation citation-type="journal">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Hubsher]]></surname>
<given-names><![CDATA[G]]></given-names>
</name>
<name>
<surname><![CDATA[Haider]]></surname>
<given-names><![CDATA[M]]></given-names>
</name>
<name>
<surname><![CDATA[Okun]]></surname>
<given-names><![CDATA[MS]]></given-names>
</name>
</person-group>
<article-title xml:lang=""><![CDATA[Amantadine: the journey from fighting flu to treating Parkinson disease]]></article-title>
<source><![CDATA[Neurology]]></source>
<year>2012</year>
<volume>78</volume>
<numero>14</numero>
<issue>14</issue>
<page-range>1096-9</page-range></nlm-citation>
</ref>
<ref id="B3">
<label>3</label><nlm-citation citation-type="book">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Kojima]]></surname>
<given-names><![CDATA[A]]></given-names>
</name>
<name>
<surname><![CDATA[Ito]]></surname>
<given-names><![CDATA[K]]></given-names>
</name>
<name>
<surname><![CDATA[Kono]]></surname>
<given-names><![CDATA[N]]></given-names>
</name>
</person-group>
<source><![CDATA[Method for production of amines and quaternary ammonium salt with adamantane skeleton]]></source>
<year>2011</year>
<publisher-name><![CDATA[Japan Patent JP 2011-051976A]]></publisher-name>
</nlm-citation>
</ref>
<ref id="B4">
<label>4</label><nlm-citation citation-type="journal">
<person-group person-group-type="author">
<name>
<surname><![CDATA[He]]></surname>
<given-names><![CDATA[JX]]></given-names>
</name>
<name>
<surname><![CDATA[Wang]]></surname>
<given-names><![CDATA[HB]]></given-names>
</name>
<name>
<surname><![CDATA[Zhou]]></surname>
<given-names><![CDATA[HY]]></given-names>
</name>
</person-group>
<article-title xml:lang=""><![CDATA[Synthesis of Amantadine Hydrochloride]]></article-title>
<source><![CDATA[Chinese Journal of Pharmaceuticals]]></source>
<year>2013</year>
<volume>44</volume>
<numero>1</numero>
<issue>1</issue>
<page-range>1-3</page-range></nlm-citation>
</ref>
<ref id="B5">
<label>5</label><nlm-citation citation-type="book">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Qiu]]></surname>
<given-names><![CDATA[Y]]></given-names>
</name>
<name>
<surname><![CDATA[Li]]></surname>
<given-names><![CDATA[L]]></given-names>
</name>
<name>
<surname><![CDATA[Wang]]></surname>
<given-names><![CDATA[J]]></given-names>
</name>
<name>
<surname><![CDATA[Wu]]></surname>
</name>
<name>
<surname><![CDATA[Lin]]></surname>
<given-names><![CDATA[Z]]></given-names>
</name>
<name>
<surname><![CDATA[Chen]]></surname>
<given-names><![CDATA[X]]></given-names>
</name>
</person-group>
<source><![CDATA[Adamantanamine hydrochloride preparation method]]></source>
<year>2013</year>
<publisher-name><![CDATA[China Patent CN 102875387A]]></publisher-name>
</nlm-citation>
</ref>
<ref id="B6">
<label>6</label><nlm-citation citation-type="journal">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Vu]]></surname>
<given-names><![CDATA[BD]]></given-names>
</name>
<name>
<surname><![CDATA[Nguyen]]></surname>
<given-names><![CDATA[VT]]></given-names>
</name>
<name>
<surname><![CDATA[Le]]></surname>
<given-names><![CDATA[TS]]></given-names>
</name>
<name>
<surname><![CDATA[Phan]]></surname>
<given-names><![CDATA[DC]]></given-names>
</name>
</person-group>
<article-title xml:lang=""><![CDATA[An Improved Synthsis of Amantadine Hydrochloride]]></article-title>
<source><![CDATA[Org. Process Res. Dev]]></source>
<year>2017</year>
<volume>21</volume>
<numero>11</numero>
<issue>11</issue>
<page-range>1758-60</page-range></nlm-citation>
</ref>
<ref id="B7">
<label>7</label><nlm-citation citation-type="journal">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Thinh]]></surname>
<given-names><![CDATA[NV]]></given-names>
</name>
<name>
<surname><![CDATA[Pham]]></surname>
<given-names><![CDATA[VH]]></given-names>
</name>
<name>
<surname><![CDATA[Vu]]></surname>
<given-names><![CDATA[BD]]></given-names>
</name>
<name>
<surname><![CDATA[Dang]]></surname>
<given-names><![CDATA[TA]]></given-names>
</name>
<name>
<surname><![CDATA[Tran]]></surname>
<given-names><![CDATA[KV]]></given-names>
</name>
<name>
<surname><![CDATA[Phan]]></surname>
<given-names><![CDATA[DC]]></given-names>
</name>
</person-group>
<article-title xml:lang=""><![CDATA[Mirowave Method for Synthesis of Amantadine Hydrochloride]]></article-title>
<source><![CDATA[Chang Mai J. Sci]]></source>
<year>2018</year>
<volume>45</volume>
<numero>6</numero>
<issue>6</issue>
<page-range>2454-8</page-range></nlm-citation>
</ref>
<ref id="B8">
<label>8</label><nlm-citation citation-type="book">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Marvin]]></surname>
<given-names><![CDATA[P]]></given-names>
</name>
<name>
<surname><![CDATA[Watts]]></surname>
<given-names><![CDATA[JC]]></given-names>
</name>
</person-group>
<collab>EI Du Pont Nemours and Co</collab>
<source><![CDATA[Pharmaceutical compositions and methods utilizing 1-aminoadamantane and its derivatives]]></source>
<year>1967</year>
<publisher-name><![CDATA[United State Patent US 3,310,469]]></publisher-name>
</nlm-citation>
</ref>
<ref id="B9">
<label>9</label><nlm-citation citation-type="">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Kraus]]></surname>
<given-names><![CDATA[GA]]></given-names>
</name>
</person-group>
<collab>Iowa State University Research Foundation (ISURF)</collab>
<source><![CDATA[Method for the synthesis of adamantane amines United State Patent US 5,599,998]]></source>
<year>1997</year>
</nlm-citation>
</ref>
<ref id="B10">
<label>10</label><nlm-citation citation-type="journal">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Shao]]></surname>
<given-names><![CDATA[G]]></given-names>
</name>
<name>
<surname><![CDATA[Yang]]></surname>
<given-names><![CDATA[M]]></given-names>
</name>
<name>
<surname><![CDATA[Wu]]></surname>
<given-names><![CDATA[C]]></given-names>
</name>
</person-group>
<article-title xml:lang=""><![CDATA[Synthesis of amantadine hydrochloride]]></article-title>
<source><![CDATA[Chemical Intermediate]]></source>
<year>2009</year>
<volume>7</volume>
<page-range>55-6</page-range></nlm-citation>
</ref>
<ref id="B11">
<label>11</label><nlm-citation citation-type="book">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Vincent]]></surname>
<given-names><![CDATA[CW]]></given-names>
</name>
<name>
<surname><![CDATA[Bruce]]></surname>
<given-names><![CDATA[AR]]></given-names>
</name>
<name>
<surname><![CDATA[Wyeth Holding]]></surname>
<given-names><![CDATA[LLC]]></given-names>
</name>
</person-group>
<source><![CDATA[Method of preparing 1-adamantanamine]]></source>
<year>1968</year>
<publisher-name><![CDATA[United State Patent US 3,388,164]]></publisher-name>
</nlm-citation>
</ref>
<ref id="B12">
<label>12</label><nlm-citation citation-type="book">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Eriks]]></surname>
<given-names><![CDATA[K]]></given-names>
</name>
<name>
<surname><![CDATA[Jack]]></surname>
<given-names><![CDATA[M]]></given-names>
</name>
<name>
<surname><![CDATA[Lilly]]></surname>
<given-names><![CDATA[Eli]]></given-names>
</name>
<name>
<surname><![CDATA[Co]]></surname>
</name>
</person-group>
<source><![CDATA[Adamantyl secondary amines]]></source>
<year>1968</year>
<publisher-name><![CDATA[United State Patent US 3,391,142 A]]></publisher-name>
</nlm-citation>
</ref>
<ref id="B13">
<label>13</label><nlm-citation citation-type="book">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Butov]]></surname>
<given-names><![CDATA[GM]]></given-names>
</name>
<name>
<surname><![CDATA[Pershin]]></surname>
<given-names><![CDATA[VV]]></given-names>
</name>
<name>
<surname><![CDATA[Burmistrov]]></surname>
<given-names><![CDATA[VV]]></given-names>
</name>
</person-group>
<collab>State educational institution of higher professional education Volgograd State Technical University (VolgSTU)</collab>
<source><![CDATA[Method of producing hydrochlorides of amine-derivatives of adamantine]]></source>
<year>2012</year>
<publisher-name><![CDATA[Russia patent RU2440971C1]]></publisher-name>
</nlm-citation>
</ref>
<ref id="B14">
<label>14</label><nlm-citation citation-type="journal">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Jirgensons]]></surname>
<given-names><![CDATA[A]]></given-names>
</name>
<name>
<surname><![CDATA[Kauss]]></surname>
<given-names><![CDATA[V]]></given-names>
</name>
<name>
<surname><![CDATA[Kalvinsh]]></surname>
<given-names><![CDATA[I]]></given-names>
</name>
<name>
<surname><![CDATA[Gold]]></surname>
<given-names><![CDATA[MR]]></given-names>
</name>
</person-group>
<article-title xml:lang=""><![CDATA[A Practical Synthesis of tert-Alkylamines via the Ritter Reaction with Chloroacetonitrile]]></article-title>
<source><![CDATA[Synthesis. 2000]]></source>
<year>2000</year>
<numero>12</numero>
<issue>12</issue>
<page-range>1709-12</page-range></nlm-citation>
</ref>
<ref id="B15">
<label>15</label><nlm-citation citation-type="book">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Schickaneder]]></surname>
<given-names><![CDATA[CP]]></given-names>
</name>
<name>
<surname><![CDATA[Hexal]]></surname>
<given-names><![CDATA[AG]]></given-names>
</name>
</person-group>
<source><![CDATA[Process for the Preparation of Adamantanamines]]></source>
<year>2009</year>
<publisher-name><![CDATA[United State Patent US 20090082596A1]]></publisher-name>
</nlm-citation>
</ref>
<ref id="B16">
<label>16</label><nlm-citation citation-type="journal">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Tsutsui]]></surname>
<given-names><![CDATA[H]]></given-names>
</name>
<name>
<surname><![CDATA[Ichikawa]]></surname>
<given-names><![CDATA[T]]></given-names>
</name>
<name>
<surname><![CDATA[Narasaka]]></surname>
<given-names><![CDATA[K]]></given-names>
</name>
</person-group>
<article-title xml:lang=""><![CDATA[Preparation of Primary Amines by the Alkylation of O-Sulfonyloximes of Benzophenone Derivatives with Grignard Reagents]]></article-title>
<source><![CDATA[Bull. Chem.Soc. Jpn]]></source>
<year>1999</year>
<volume>72</volume>
<numero>8</numero>
<issue>8</issue>
<page-range>1869-78</page-range></nlm-citation>
</ref>
<ref id="B17">
<label>17</label><nlm-citation citation-type="journal">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Kitamura]]></surname>
<given-names><![CDATA[M]]></given-names>
</name>
<name>
<surname><![CDATA[Chiba]]></surname>
<given-names><![CDATA[S]]></given-names>
</name>
<name>
<surname><![CDATA[Narasaka]]></surname>
<given-names><![CDATA[K]]></given-names>
</name>
</person-group>
<article-title xml:lang=""><![CDATA[Synthesis of primary amines and N-methylamines by the electrophilic amination of grignard reagents with 2-imidazolidinone O-sulfonyloxime]]></article-title>
<source><![CDATA[Bull. Chem.Soc. Jpn]]></source>
<year>2003</year>
<volume>76</volume>
<numero>5</numero>
<issue>5</issue>
<page-range>1063-70</page-range></nlm-citation>
</ref>
<ref id="B18">
<label>18</label><nlm-citation citation-type="journal">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Kitamura]]></surname>
<given-names><![CDATA[M]]></given-names>
</name>
<name>
<surname><![CDATA[Suga]]></surname>
<given-names><![CDATA[T]]></given-names>
</name>
<name>
<surname><![CDATA[Chiba]]></surname>
<given-names><![CDATA[S]]></given-names>
</name>
<name>
<surname><![CDATA[Narasaka]]></surname>
<given-names><![CDATA[K]]></given-names>
</name>
</person-group>
<article-title xml:lang=""><![CDATA[Synthesis of Primary Amines by the Electrophilic Amination of Grignard Reagents with 1,3-Dioxolan-2-one O-Sulfonyloxime]]></article-title>
<source><![CDATA[Org. Lett]]></source>
<year>2004</year>
<volume>6</volume>
<numero>24</numero>
<issue>24</issue>
<page-range>4619-21</page-range></nlm-citation>
</ref>
<ref id="B19">
<label>19</label><nlm-citation citation-type="book">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Zhang]]></surname>
<given-names><![CDATA[Z]]></given-names>
</name>
</person-group>
<source><![CDATA[Synthesis method for Amantadine Hydrochloride]]></source>
<year>2011</year>
<publisher-name><![CDATA[China Patent CN 102050744B]]></publisher-name>
</nlm-citation>
</ref>
<ref id="B20">
<label>20</label><nlm-citation citation-type="journal">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Stetter]]></surname>
<given-names><![CDATA[H]]></given-names>
</name>
<name>
<surname><![CDATA[Mayer]]></surname>
<given-names><![CDATA[J]]></given-names>
</name>
<name>
<surname><![CDATA[Schwarz]]></surname>
<given-names><![CDATA[M]]></given-names>
</name>
<name>
<surname><![CDATA[Wulff]]></surname>
<given-names><![CDATA[K]]></given-names>
</name>
</person-group>
<article-title xml:lang=""><![CDATA[Über Verbindungen mit Urotropin-Struktur, XVI. Beiträge zur Chemie der Adamantyl-(1)-Derivate]]></article-title>
<source><![CDATA[Eur. J. Inorg. Chem]]></source>
<year>1960</year>
<volume>93</volume>
<numero>1</numero>
<issue>1</issue>
<page-range>226-30</page-range></nlm-citation>
</ref>
<ref id="B21">
<label>21</label><nlm-citation citation-type="journal">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Moiseev]]></surname>
<given-names><![CDATA[IK]]></given-names>
</name>
<name>
<surname><![CDATA[Doroshenko]]></surname>
<given-names><![CDATA[RI]]></given-names>
</name>
<name>
<surname><![CDATA[Ivanova]]></surname>
<given-names><![CDATA[VI]]></given-names>
</name>
</person-group>
<article-title xml:lang=""><![CDATA[Synthesis of amantadine through medium of nitrate 1-adamantanol]]></article-title>
<source><![CDATA[Pharm. Chem. J]]></source>
<year>1976</year>
<volume>10</volume>
<page-range>450-1</page-range></nlm-citation>
</ref>
<ref id="B22">
<label>22</label><nlm-citation citation-type="book">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Periandy]]></surname>
<given-names><![CDATA[N]]></given-names>
</name>
<name>
<surname><![CDATA[Kilaru]]></surname>
<given-names><![CDATA[S]]></given-names>
</name>
<name>
<surname><![CDATA[Thennati]]></surname>
<given-names><![CDATA[R]]></given-names>
</name>
</person-group>
<source><![CDATA[Novel process for the preparation of aminoadamantane derivatives]]></source>
<year>2005</year>
<publisher-name><![CDATA[World Intellectual Property Organization Patent WO2005062724 A2]]></publisher-name>
</nlm-citation>
</ref>
<ref id="B23">
<label>23</label><nlm-citation citation-type="book">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Wolfgang]]></surname>
<given-names><![CDATA[H]]></given-names>
</name>
</person-group>
<source><![CDATA[Studiengesellschaft Kohle mbH, assignee. Process for the production of N-tert-alkyl amides and, if desired, N-tert. alkyl amines]]></source>
<year>1964</year>
<publisher-name><![CDATA[United State patent US 3,152,180]]></publisher-name>
</nlm-citation>
</ref>
<ref id="B24">
<label>24</label><nlm-citation citation-type="book">
<person-group person-group-type="author">
<name>
<surname><![CDATA[Yao]]></surname>
<given-names><![CDATA[F]]></given-names>
</name>
<name>
<surname><![CDATA[Xie]]></surname>
<given-names><![CDATA[L]]></given-names>
</name>
<name>
<surname><![CDATA[Guo]]></surname>
<given-names><![CDATA[YF]]></given-names>
</name>
</person-group>
<source><![CDATA[Synthetic method of adamantanamine hydrochloride]]></source>
<year>2016</year>
<publisher-name><![CDATA[China Patents CN105294445A]]></publisher-name>
</nlm-citation>
</ref>
</ref-list>
</back>
</article>
