BE629218A - - Google Patents

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Publication number
BE629218A
BE629218A BE629218DA BE629218A BE 629218 A BE629218 A BE 629218A BE 629218D A BE629218D A BE 629218DA BE 629218 A BE629218 A BE 629218A
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BE
Belgium
Prior art keywords
desc
page number
clms page
acid
water
Prior art date
Application number
Other languages
French (fr)
Publication of BE629218A publication Critical patent/BE629218A/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

       

   <Desc/Clms Page number 1> 
 
 EMI1.1 
 



  "Prooédé de préparation de compos4a de d1,hénylpyr1d1ntmétho.nt". 
 EMI1.2 
 



  141 présenta invention  ni relative à un nouveau procédé et jusqu'à présent Inconnu pus-ir In ..rJ..ut't1Qn de tJ::tp()..n de d1phénylllyr1drlV1t='thnne. 0(4,pocêd ont rdao ,.Q.mt été utU1e6", dans une l r|Ç9 C1tUlurt,;. ',AYAaA.al1 3YY111.e.:k t}iéru,!:\JtiU.ZI8f en par- t1eu11tr cor.%* dÓ81nfQotntfi et 90": 1t1!5. 



  .ad rdddd connu  pour la .rér-a1"IJ.t.i'î" je dubatuncea de n type sont Mnl'...l4J!tJfJnt Innée rlar J, ,;:rld1nu (tldëftyde ou sur la pyyi<UM cétone, êubnti tao, di besoin est, dune le noyau de la 1.yrid.1f,. ces Bubstanomt êtunt or,dnde8 avec de  phénol  en présence d'ubnorbanta. 



  Tout. toit . l'inconvénient que prédantsnt con procédés *et que coule des oor-1-ondn leuvent hn frér.i4.1'ée p;.r ce  pro- céd41S, datie leequtlb les ;1to'x NUt1B j.hény3  *ont k la roie 

 <Desc/Clms Page number 2> 

 
 EMI2.1 
 substituée ou Identiquement substitués puiaqu'il  et 1mpou81 
 EMI2.2 
 de cette façon  d'obtenir une substitution dissymétrique dans ces groupes. 



  Le procédé conforme à l'invention est approprié en parti- 
 EMI2.3 
 culier à la préparation de composés d'aminodiphénylpyr1dylméth ne, aussi bien que de composés d'hydroxydiphénylpyridylméthanel parce que la déméthylation, la diazotation et le remplacement du groupe diazonium piir OH, etc# peuvent dtre réalisé  au moyen d'amonts de cotidonniition spéciaux# pur exemple due mélanges d'(1Q1dl:t oulfurlque oOI1Qf)ntrd et demup oura  épuration des ln.. toradiaiyfc. 



  Ima OOlllIJ08éij de divll1n'yll)'yrid,ylmdthbtus liréiturde oonfar-' 1II,s.lIîJUt 1\11 l'N(J{,dl   Ion 1... lll'dttl,utfl invention  ont U}I'11161 en général ptir la formule suivante! 
 EMI2.4 
 
 EMI2.5 
 dana 1uquolle X représente un ittome d'hydrogène ou d'halog9nt ou un groupe alcoyle, hydroxy, 0.100X1. aryle, aIa'Uc11., nitro, $mina, acide aultonique ou acyloxy, Z représente un atoze d'hy- drogènt ou un groupe alooyle ou un atome d'halogène et Y repré- conte un groupe Misino ou un groupe hydroxy* Le procédé conforme à l'invention  1; en substance cars0j l.tSr1eê par la condensation d'un phér:ylpyr1d.rluuH:hanol ,xlir1r  en général par la forzule suivante;

   

 <Desc/Clms Page number 3> 

 
 EMI3.1 
 
 EMI3.2 
 clan. laqua 11* X  t 2 ont la r.8:> t ttig1J1ticution çu c1-def.l"U8, tn prl*eno  d'en ant de 6prùtion d'eau, avec un oompoaé taiao r4ndLt la formule &éndr8Î i 
 EMI3.3 
 
 EMI3.4 
 dans laquelle X rorrècetitu un t%tome d'Kyvtrogène ou à'hsslct,e ou un group  aloo11o hyJroxy, itlcoxjr  arylet etrMixylWt l> Mi no ou .)'1f,)X1, }luit..-!,u' aU\1un atoae d '1\)'JrQI :t M doit ttro dune la l'oa1 tion . para pur l'nI l'or1- u. , un frvujo hydruxyt aloosy ou Myloxy, et fl r<tj)'y!!)<'n<.a un gr0\11'O ur.x1tw 1,r11t11"o f 8fJCDndait'f.' ou tertiaire* Si Y, ost un arvv; u...tno N'i'.2J'., 1. produit de condfJuol.\t1on n,1t11;t1 obtenu tut, pi lCif!,1tt ont, dure 1A. et le I/:rOu1'''' 111M()n1ul'' rmt:uca JIll" un f-ruiipa 3y.ârc,y  un  ae.snic do l'1u1.ul'!I1thU"i t'.. lorB do Ilutlllontioti du )'r'Ocêl.1tl 11f1 t1U'j:)til.m.

   MU lieu de phénol pour le 1\rQ(H,tû do p0t;d !;fnti<:)n, unv td pl1 tien U,)fi 1..... portant  de n tcehnjLt)uo unt.é'hlu'" .H1t ('1:)HOUIt ¯l!It r<uîl8 J   lttquol1w .. été â4saontr## fnr 1'or16n h lR iTct  au *tft4  du laboratoire eut au "tt4l1(t d'une production à ftundio I,'he 118..n (>titre# de plue I{t'M\t" rrt. ,,tt  ont Ob\ttt1\t 1oIit"'Of I,l-,icëd4p tel que cool nnu:1'ah. dan  lon fS,Jr,:.11)1ot' ,1,:'1\1,('$ o:1"I'J'r.. 

 <Desc/Clms Page number 4> 

 
 EMI4.1 
 



  Contor=6::umt è. l'invention, tout agent absorbant :1. -.au, communémont utilisa dans ce tout  peut <tre employé ooaae *gent de séparation d'eau, tel que l'acide eulturîqueo l'ttoidedhtiop- hyrique concentrât le chlorure de zinrl l' 601<1,1 pho'rhor1qb.., i le chlorure stannique ou des composas 11;n11a1r... 
 EMI4.2 
 



  L'invention est illustrée par des exemples et décrite en détail ci-après, 
 EMI4.3 
 LZ lut LI y.Qi'tio de 4T|'rQx:y?4 ft*4iO?4At?Vrçylvr4'rfft"'1ff(Hf1*1lt* Un méltu-sko de 10 g. de p   Sthoxy}'h*nylpyri<3yl¯2-  'thanol*1 de 10 g. d'aniline et de 50 ml. d'acide oulturique à 50 est chautfé au reflux penlunt 6 huures. Aprbe r.tro1d1.ftem", le mdlane& rt-uctluntiol omt dilue dans lOu ?1. d'eau et lit valeur du pli est réglée h environ 6 nu moyen d'une solution d'hydroxy- de de sodium à 10.

   Le prêché formé est e6rar' et reori t lUe4| dans de l'éthanol à 50' Rendemointi 11 go de 4-=6 tboxl-4 ' -"'1110-] diphénylpyrid,yl-2-métlianto Ce composé  qui n'n pas été décrit antérieurement dans lit littérature  se présente tout la tome de erietaux pr1nmat1qtHH' incolore   dont le point de l'union *et de 120 à 12100# }laide moléculaire déterminéi 292 - théoriquement) 
 EMI4.4 
 290,26. 
 EMI4.5 
 



  EM.M.1" l'X, jjJB.ar.tl 9 q . , à, e # 4 r-Y 1y 9 iHY "4.*? W <t. Bffl'l>.B îfl BJt l>.ltfiyJtTiR"i4 1 ?i.ttfl<f.* 6#45 go de p-sjéUioxyphdnylpyridyl 2- 4thanol et 2 ta gt d'unilinq cont dissous dans 25 Mit d'acide su 1 fur i que a 50% et le mélange est chauffé nu reflux pendant 6 heures 1 mélange renotionnel ont refroidi légbrlSrnont et. 9 aï, d'acide bi'omhydri'- que z 60% sont ajoutée, après quoi 3't cluluft8te au reflux est poursuivi poridnnt 5 heures. Apt'l<a retrcHd1e/'ltltJ1(Jnt, le mélange 
 EMI4.6 
 est dilué dans 50 ml. d'eau et l'acide est. neutralisé au moyen 
 EMI4.7 
 d'une solution d'hydroxyde de 80ùiua h 10, 1. précipité formé est .tCSIf!2'\ et peut 8tre purifie pur t'1JoriotuHi...1.1on datie de 

 <Desc/Clms Page number 5> 

 
 EMI5.1 
 Ilithanol dilué.

   Le 4 hydrQxy 4'-arain0diph *nyîpyridyl-2  <Hh*n  Obtenu ont une aubatunce 1noolol'fI  e co:'j9a!'t ". orhh,1.\1 eon"<K)tyieHquwN oo1.Qp,ormUX et. tlthuh.1.rf#lh dt!ut. le point de tua1ot. % l de 100 à 11)10(; (déûau-ition)* 4'oide moléculaire dêtormînéi 201   théoriquement! 278,23. 



  Rendement! 5,8 du .4t'.-hyVK.YlMA'.YCi.')!:-2.<M' 6,45 g. de J".Ul6tlw.i'lJJjÚI'yJiJ1.t'l'J'y1...;?...,Sthl.l.t)t)l, 2,6 j'{. d'aniliaii et 2 -MI, d'ucid   Kifr!'}' fe 0 "unt, Q}lItl1fN....u reflux !"rl\:So.n 13 )1II\u'"n. J.cH "'lUI1 !#  ltilSlL>TllI,Y agit J6p'I)r.I,"f'fI .('(1. troid1. 9ml* d'ueids brMhydriqM à 60}  Mit  jouté  <tu mélange et le chauttugct au reflux ont l;ou1'8u1 vi pondant 5 heures. Aprh le CQn'l"'I1,,(.f\r de reflux $et enlevé et le bü.l1Dn de réaction est pl;Ào4 Aur un bain de 1rMe.

   A l'aide d'un en- tonuoir $épnr6t une tHJ1J\':!rJU û*t ,2 go de nitrite de 80111\1IA dane 10 ml. d'eau ont ajoutée pendant 5 minutée environ et boue alitutîon ccnfttnte< Le mélange ré,tct1o/'tf.el est nolencume- ment vIre' dan4 25 ml. d'aolde sulfurique bouillant h 25- et le mélange est maintenu uu point d'Al.ull1t1on pendant une demi-heure  14 mélane est refroidie t gr(C fi. quoi un précipite brungtre est formé  et le liqulde est sépara par t11tration. 



  A partir du liquide kc1de, lot 4t4'-dihydroxydipMnylpyridyl--2-' 116th on6 cet pr60i l-ité soue 1& forso d'une poudre j: .un4 tr(1 au moyen d'un  solution d'hy;ytruxyde de flod1um 1.. 1(. Une ilue grande quantité de 4t4'-dihydroxydi];h<'y.yridyl'-2'-(!t!ttan< peut Stre obtenue i. partir du lrclrH6 brun/an. L9 p'éI'}1plt.ti est d1,uH\1' dans une h .c , l1p'ètf fluai lu solution est uc1ditUe. 



  Après filtration, la substance cet Irtcl11t' oozr-e 01-denous au moyen d'une solution dehydroxyde de sodium lujC. 



  It produit a un point de fusion de 210-21500 et le dérivé dia- 

 <Desc/Clms Page number 6> 

 
 EMI6.1 
 citYlO z un Point de tueïon do 1?4-135'0< Rendementi 4$55 go oryompndttnt & ':5% du. rendemont 'th6or1qut. 



  1Ui.'±.tiIQAnWi. l'Irooc14ô de 1 :r6pax'ation de componée de dîplidnylpyrldylmi- thane exprima par la formule gènérale ci-aprées 
 EMI6.2 
 
 EMI6.3 
 dan, laquelle X représente un atome d'hydrogène ou d'halogène ou. un groupe alooyleo hydroxy, uloOX1. aryle, aralkylet nitro, amînoo acide aultonique ou acyloxys Z représente un ¯to#'h1. drogêne ou un groupe alcoyle ou un atome d 'halo,%e, et Y re- présente un groupe amino ou un groupe hydroxy, oaract'r1e' pax la condensation d'un phén'ylp'yr1dylmÓtlanol exprimé par la foi,- 
 EMI6.4 
 mule générale! 
 EMI6.5 
 

**ATTENTION** fin du champ DESC peut contenir debut de CLMS **.



   <Desc / Clms Page number 1>
 
 EMI1.1
 



  "Process for the preparation of d1, hénylpyr1d1ntmétho.nt compos4a".
 EMI1.2
 



  141 presenta invention nor relating to a new process and until now Unknown pus-ir In ..rJ..ut't1Qn of tJ :: tp () .. n of d1phenylllyr1drlV1t = 'thnne. 0 (4, pocêd ont rdao, .Q.mt been utU1e6 ", in a lr | Ç9 C1tUlurt,;. ', AYAaA.al1 3YY111.e.:ktariensiéru,!:\JtiU.ZI8f in par- t1eu11tr cor .% * dÓ81nfQotntfi and 90 ": 1t1! 5.



  .ad rdddd known for the .rér-a1 "IJ.t.i'î" I dubatuncea of n type are Mnl '... l4J! tJfJnt Innate rlar J,,;: rld1nu (tldëftyde or on the pyyi <UM ketone , éubnti tao, di need is, dune the nucleus of 1.yrid.1f ,. these Bubstanomt etunt gold, dnde8 with phenol in the presence of ubnorbanta.



  All. roof. the disadvantage that predantsnt con processes * and that oor-1-ondn flows have hn frér.i4.1'ée p; .r this process41S, datie leequtlb les; 1to'x NUt1B j.hény3 * have k la king

 <Desc / Clms Page number 2>

 
 EMI2.1
 substituted or Identically substituted since he and 1mpou81
 EMI2.2
 in this way to obtain an asymmetric substitution in these groups.



  The process according to the invention is particularly suitable.
 EMI2.3
 cular in the preparation of aminodiphenylpyridylmeth ne compounds, as well as hydroxydiphenylpyridylmethanel compounds because demethylation, diazotization and replacement of the diazonium piir OH group, etc # can be achieved by means of special cotination fillers # pure example of mixtures of (1Q1dl: t oulfurlque oOI1Qf) ntrd and demup oura purification of ln .. toradiaiyfc.



  Ima OOlllIJ08éij de divll1n'yll) 'yrid, ylmdthbtus liréiturde oonfar-' 1II, s.lIîJUt 1 \ 11 l'N (J {, dl Ion 1 ... lll'dttl, utfl invention have U} I'11161 in general choose the following formula!
 EMI2.4
 
 EMI2.5
 dana 1uquolle X represents a hydrogen or halogen atom or an alkyl, hydroxy, 0.100X1 group. aryl, ala'Uc11., nitro, $ mina, aultonic acid or acyloxy, Z represents a hydrogen atom or an alooyl group or a halogen atom and Y represents a misino group or a hydroxy group * method according to the invention 1; in substance cars0j l.tSr1eê by the condensation of a pher: ylpyr1d.rluuH: hanol, xlir1r in general by the following formula;

   

 <Desc / Clms Page number 3>

 
 EMI3.1
 
 EMI3.2
 clan. laqua 11 * X t 2 have r.8:> t ttig1J1ticution çu c1-def.l "U8, tn prl * eno eno enant de 6prùtion of water, with an oompoaé taiao r4ndLt the formula & éndr8Î i
 EMI3.3
 
 EMI3.4
 in which X rorrècetitu a t% tome d'Kyvtrogène or à'hsslct, e or an aloo11o hyJroxy group, itlcoxjr arylet etrMixylWt l> Mi no or.) '1f,) X1,} luit ..- !, u' aU \ 1a atoae d '1 \)' JrQI: t M must ttro dune la oa1 tion. para pur l'nI or1- u. , a hydruxyt aloosy or Myloxy frvujo, and fl r <tj) 'y !!) <' n <. has a gr0 \ 11'O ur.x1tw 1, r11t11 "o f 8fJCDndait'f. ' or tertiary * If Y, ost un arvv; u ... tno N'i'.2J '., 1. product of condfJuol. \ t1on n, 1t11; t1 obtained tut, pi lCif !, 1tt have, lasts 1A. and the I /: rOu1 '' '' 111M () n1ul '' rmt: uca JIll "un f-ruiipa 3y.ârc, y un ae.snic do l'1u1.ul '! I1thU" i t' .. lorB do Ilutlllontioti du) 'r'Ocêl.1tl 11f1 t1U'j:) til.m.

   MU place of phenol for 1 \ rQ (H, tû do p0t; d!; Fnti <:) n, unv td pl1 tien U,) fi 1 ..... bearing de n tcehnjLt) uo unt.é'hlu '".H1t (' 1:) HOUIt ¯l! It r <uîl8 J lttquol1w .. summer â4saontr ## fnr 1'or16n h lR iTct at * tft4 of the laboratory had at" tt4l1 (t of a production at ftundio I , 'he 118..n (> title # of plus I {t'M \ t "rrt. ,, tt have Ob \ ttt1 \ t 1oIit"' Of I, l-, icëd4p such as cool nnu: 1'ah . dan lon fS, Jr,:. 11) 1ot ', 1,:' 1 \ 1, ('$ o: 1 "I'J'r ..

 <Desc / Clms Page number 4>

 
 EMI4.1
 



  Contor = 6 :: umt è. invention, any absorbent agent: 1. -.au, commonly used in this all can <be employed ooaae * gent of water separation, such as eulturic acidoidedhtiophyric acid concentrated zinrl chloride 601 <1.1 pho'rhor1qb .. , i stannic chloride or compounds 11; n11a1r ...
 EMI4.2
 



  The invention is illustrated by examples and described in detail below,
 EMI4.3
 LZ read LI y.Qi'tio de 4T | 'rQx: y? 4 ft * 4iO? 4At? Vrçylvr4'rfft "' 1ff (Hf1 * 1lt * A 10 g Méltu-sko of p Sthoxy} 'h * nylpyri <3yl¯2- 'thanol * 1 of 10 g. Of aniline and 50 ml. Of ulturic acid at 50 is heated at reflux penlunt 6 huures. Aprbe r.tro1d1.ftem ", mdlane & rt-uctluntiol omt dilute in 10 µl of water and the fold value is set to about 6 µl on average of 10% sodium hydroxide solution.

   The formed sermon is e6rar 'and reori t lUe4 | in ethanol at 50 'Rendemointi 11 go of 4- = 6 tboxl-4' - "'1110-] diphenylpyrid, yl-2-metlianto This compound which has not been previously described in the literature presents all the tome de erietaux pr1nmat1qtHH 'colorless with the union point * and from 120 to 12100 #} molecular uid determinedi 292 - theoretically)
 EMI4.4
 290.26.
 EMI4.5
 



  EM.M.1 "l'X, jjJB.ar.tl 9 q., To, e # 4 r-Y 1y 9 iHY" 4. *? W <t. Bffl'l> .B îfl BJt l> .ltfiyJtTiR "i4 1? I.ttfl <f. * 6 # 45 go of p-sjéUioxyphdnylpyridyl 2- 4thanol and 2 ta gt of unilinq cont dissolved in 25 ml of su acid 1 to 50% and the mixture is heated under reflux for 6 hours 1 renotional mixture has cooled lightly and 9% of 60% biomhydric acid is added, after which 3 'cluluft8te au reflux is continued for 5 hours. Apt'l <a retrcHd1e / 'ltltJ1 (Jnt, the mixture
 EMI4.6
 is diluted in 50 ml. of water and the acid is. neutralized by means
 EMI4.7
 of a hydroxide solution of 80ùiua h 10, 1. the precipitate formed is .tCSIf! 2 '\ and can be purified pure t'1JoriotuHi ... 1.1on date of

 <Desc / Clms Page number 5>

 
 EMI5.1
 Diluted ilithanol.

   The 4 hydrQxy 4'-arain0diph * nyîpyridyl-2 <Hh * n Obtained have an aubatunce 1noolol'fI e co: 'j9a!' T ". Orhh, 1. \ 1 eon" <K) tyieHquwN oo1.Qp, ormUX and . tlthuh.1.rf # lh dt! ut. the point of tua1ot. % l from 100 to 11) 10 (; (deûau-ition) * 4'detorminei molecular acid 201 theoretically! 278.23.



  Yield! 5.8 of .4t '.- hyVK.YlMA'.YCi.')!: - 2. <M '6.45 g. de J ".Ul6tlw.i'lJJjÚI'yJiJ1.t'l'J'y1 ...;? ..., Sthl.lt) t) l, 2.6 j '{. aniliaii and 2 -MI , d'ucid Kifr! '}' fe 0 "unt, Q} lItl1fN .... u reflux!" rl \: So.n 13) 1II \ u '"n. J.cH "'lUI1! # LtilSlL> TllI, Y acts J6p'I) rI," f'fI. (' (1. Troid1. 9ml * of ueids brMhydriqM at 60} Mit jouté <you mix and chauttugct with The reflux was 1 or 8u1 for 5 hours. After the reflux was removed and the reaction bü.l1Dn was taken into a 1rMe bath.

   With the aid of a stent, 2 g of 80111 \ 1IA nitrite in 10 ml. of water were added for about 5 minutes and sludge alitution continued <The mixture was completely darkened in 25 ml. boiling sulfuric acid 25 hours and the mixture is kept at the Al.boiling point for half an hour. The mixture is cooled to gr (whereby a brownish precipitate is formed and the liquid is separated by filtration.



  From the liquid kc1de, lot 4t4'-dihydroxydipMnylpyridyl - 2- '116th on6 this pr60i l-ity is 1 & forso of a powder j: .un4 tr (1 by means of a solution of flod1um hytruxide 1 .. 1 (. A large amount of 4t4'-dihydroxydi]; h <'y.yridyl'-2' - (! T! Ttan <can be obtained from brown lrclrH6 / year. L9 p'eI '} 1plt.ti is d1, uH \ 1' in a h .c, l1p'étf fluai read solution is uc1ditUe.



  After filtration, the substance is removed from us by means of a lujC sodium hydroxide solution.



  It product has a melting point of 210-21500 and the derivative dia-

 <Desc / Clms Page number 6>

 
 EMI6.1
 citYlO z un Kill Point do 1? 4-135'0 <Yieldi 4 $ 55 go oryompndttnt & ': 5% of. rendemont 'theor1qut.



  1Ui. '± .tiIQAnWi. Irooc146 of 1: repaxation of compound of dlplidnylpyrldylmythne expressed by the general formula below
 EMI6.2
 
 EMI6.3
 dan, wherein X represents a hydrogen or halogen atom or. an alooyleo hydroxy group, uloOX1. aryl, aralkyl and nitro, aminoo aultonic acid or acyloxys Z represents a ¯to # 'h1. drogen or an alkyl group or a halo atom,% e, and Y represents an amino group or a hydroxy group, aract'r1e 'pax the condensation of a phenylp'yr1dylmÓtlanol expressed by the faith, -
 EMI6.4
 general mule!
 EMI6.5
 

** ATTENTION ** end of DESC field can contain start of CLMS **.

Claims (1)

EMI6.6 dôme laquelle X et t ont la meat sienitication que o1-4e.lu8, en présente d'un agent de Ivaration d'eau, avec un composé amino répondant z la for%ut général* <Desc/Clms Page number 7> EMI7.1 EMI7.2 dane 1aqu.lh :x fwpft'ief'ntt! un n\,)1r. .1t:.y,!r'}r.h. ou dthu.log1me ou, un troup. uloOl1. h,y,1rox)'. nlcnxy, nry10. urulkyler )M5in<? 011 ac)'loJ'1' l1uie1\\tnuun ato!:,<t à'nyJryî-f 9 11/# don '\rtf dW18 le, Fod \ion parA par rn; pr:1"t 1, un fT'0ar'-;> }.,yl1roxy..,ll1ox,y ou aOl1ox;, <t T rrprésonte un ru 1r.o r1ur.. G'onda1re ou %trti iir i et ri Y cat un fr\,ú. uïl ;u .-=zi,.. re le ro- duit dn sn,3trtutitt AlfHt1 octenu r,"'Jt. ni lH:tf1p1n u8t, 4tr dla:ot6 .1 rtchaJjtt6 ftant* eéj'arHtion .11.", 1nt",1':'11.:<11a1",. EMI6.6 dome which X and t have the meat sienitication that o1-4e.lu8, by presenting a water ivaration agent, with an amino compound corresponding to the general strength * <Desc / Clms Page number 7> EMI7.1 EMI7.2 dane 1aqu.lh: x fwpft'ief'ntt! a n \,) 1r. .1t: .y,! R '} r.h. or dthu.log1me or, a herd. uloOl1. h, y, 1rox) '. nlcnxy, nry10. urulkyler) M5in <? 011 ac) 'loJ'1' l1uie1 \\ tnuun ato!:, <T à'nyJryî-f 9 11 / # don '\ rtf dW18 le, Fod \ ion parA by rn; pr: 1 "t 1, un fT'0ar '-;>}., yl1roxy .., ll1ox, y or aOl1ox ;, <t T r represents a ru 1r.o r1ur .. G'onda1re or% trti iir i and ri Y cat un fr \, ú. uïl; u .- = zi, .. re the reduct dn sn, 3trtutitt AlfHt1 octenu r, "'Jt. ni lH: tf1p1n u8t, 4tr dla: ot6 .1 rtchaJjtt6 ftant * eéj'arHtion .11. ", 1nt", 1 ':' 11.:<11a1 ",.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2034506A1 (en) * 1969-01-29 1970-12-11 Thomae Gmbh Dr K

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2034506A1 (en) * 1969-01-29 1970-12-11 Thomae Gmbh Dr K

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