HUE029970T2 - Eljárás SGLT2 inhibitorok elõállítására - Google Patents

Eljárás SGLT2 inhibitorok elõállítására Download PDF

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HUE029970T2
HUE029970T2 HUE09808859A HUE09808859A HUE029970T2 HU E029970 T2 HUE029970 T2 HU E029970T2 HU E09808859 A HUE09808859 A HU E09808859A HU E09808859 A HUE09808859 A HU E09808859A HU E029970 T2 HUE029970 T2 HU E029970T2
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alkyl
chloro
benzyl
group
phenyl
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HUE09808859A
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Jason Liou
Yuelin Wu
Shengbin Li
Ge Xu
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Theracos Sub Llc
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    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • A—HUMAN NECESSITIES
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
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    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
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    • C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
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    • C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
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    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
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    • C07H7/04—Carbocyclic radicals

Claims (4)

  1. Szabadalmi igénypontok I, BîjÂiIA képleté komplex; (ÏA) képlet
    rtanurmsav)« (ΊΑ) almi ax η értéke 1 vagy 1 R1 jelentését a hídmgéB, Mkgén es a Cp^alkiícsepőrt alkötta esoportból válászfjbk; V jelentését az oxigén és az egyes kötés alkotta csoportból választ]uk; W jelentéséi az alábbiak által alkotott csoportból választjuk: Cr€« alkiîén, CrCs aikébiiiB, €-2-0(,álktólén, Cj-Cîôcíkloalkilén, és (€3-(¾eikloalkUén)^(C}-CAalkilén); X jelentését az oxigén, az egyes kötés és MRfl alkotta csoportból válásijuk; és Y jelentését az alábbiak által alkotott csoportból választjuk; hidrogén, CrQ, alkií, Q-Cg haiogép-alkil, Gj-Cg hldroxi-alkjijCs^Cls alkénlh €$-€$ tiktól·, Cj-Cjó eikloaikiktCaAoo cîkloalkü l-Cj-C* alkií, (C1-C4 alkü~oxx)-Ci-|3j tiki!, (Cj-Cjo .ciModläl-oxlVÖrtö aîkll, ijanúnoj-Ci-Oj alkií, {C5-C4 alkil-ammoVCrCa alkií, (Cy-Cg alkíI}-kafhooih alk.emI)~karbonil, (CrQ alklniO-karbonií, (CrCg alkiíFszulfoniL alkenilj- -szül tonik és (C:>'C(i aikinilVszulfoml, aboi W, X es Y alkií-, alkom!-, alkinil- és cikloalkilcsoportjal vagy részei adott esetben részlegesen vagy teljesen ílnoroxottak és adott esetben a klór, hidroxi-, Cj-Q alkií-, €\~Q alkoxí~s és C3-Q cikloalkílesoportok közit! választott azonos vagy különböző szubsztituenssel mono- vagy díszubsztltutáltak, és a cikioalkiIcsoporiokhan vagy részekben egy vagy két metiléncsöportní: adott esetben egymástól függetlenül (X S, CO, SO, SO2 vagy MRb helyettesít, és egy vagy több metiléncsoportot adott esetben N helyettesít; :Ra jelentését egymástól függetlenül az alábbiakból álló csoportból választjuk: II, CrCft eikloalkíi és {Cj-Ch alkiífkarbonil, ahol az alk.il- és eikloalkilcsoportök vagy ri-szék adott esetben részlegesen vagy teljesen íluorozottak; mindegyikének jelentését egymástól függetlenül az alábbiakból álló csoportból választ-jak: FI, C;-C4 alkií és (C3-C4 alfcíO-karboml, ahol az alkilcsoportok vagy részek adott esetben részlegesen vagy teljesen íluorozottak; vagy annak gyógyszerészedléi elíOgádbátói:sót előállítására; amely magában foglalja: •(a) II képletű. vegyidet reagáltatását
    00 sperre) egy aktiváló csoport jelenlétében III képletű vegyölet kialakítására
    OH); és (b) a 111 képiéin vegyidet érintkezésbe hozását egy atniaosavval m ÍA képiéin komplex kialakítására; ahol az (a) és (b) lépéseket a Ili. képiéül vegyüiet tisztítása nélkül végezzük és ahol az (a) és (b) lépéseket egymás Ä végezzük vMtopiÉáit ÂbéiMiWt'. azok etóvoiítási lépése nélkül.
  2. 2. Az 1, igénypont szerinti. ellátás, ahol az eljárást egyetlen reakeiőedénybeft végezzük. 3. A 2. igénypont szerinti eljárás, ahol az IÁ képiéta komplexét kristályos szilárd abyigkoatázöllljúk,
  3. 4. Az 1, igénypont, szerinti eljárás, ahoi a redukáló szer egy alkil-sziHl-hidrid és az aktiváló szer egy Lewis sav. §. A 4. igénypont szerinti eljárás, ahol a redukáló szer trieul-sziláa és a Lewis sav BFj Et20. i. Az 1. igénypont szerinti eljárás, ahol az (a) lépési az alábbi ésopörtböl választeít oldószerben* aeetonítril és diklór-rnetán, vagy ezen oldószerek keverlkében végezzük.
  4. 7, Az 1, igénypont szerinti eljárás, ahol a (b) lépést az alábbi esopordíól v^asztott oldószerben; etanol, viz és békán, vagy ezen oldószerek keverékében végezzük, §, Az 1. igénypont szerinti eljárás, ahol az IA képletű komplex az alábbi vegyük-íek csoportjából választott vegyüiek ('2S,3R!4R!5S!óR)~2-(4“klőr-3~(4-(2"{2~metoxi''etoxí)-eloxi)'-benzíl}~íénil)"ó^b:idroxi'-met:il'Híet-rahidro~2 II ~pi rá.u-3,4,5 -triói; {2S,3R,4R,5S,óR)-2-';3-(4»(2-taHi!“OXÍ)-etoxi)-benzil)-4~klőr-fénil)~ó-(hidroxi~metil)-tctTahidro~ -2H»pimn-3,4,5~tríoí; (2S,3R,4R,5S,óR>2~(4»k.iór»3-(4-(2~(prop-2~inií-oxi)-etoxi)”benzil}-íénil)-ó»^tiröxnínetilj»tet* tahi dro« 2H -pirámS ,4,5 "triói; (2S3FV.4R,5S,6R)-2"(4~kIór'3-(4--(1 (pfop'-2-'iriil-'Oxi)-'propai'-“2“il~oxiVbenzi 1)--10(¾ l)--6'(hidroxs· (2S53Rí^R->5S!6R)'2~(4“kiár“3'-(4'-(43iidrox?~b«í'-2-'ínil-oxí)-benzil)-fenií)-6~(hi<Íroxi"metü)~íet- rahidro~2H»pir#^|:^4H^i#!i:; (2S3R.4R, 5 S s6 R)-2-í 4-ki ór- 3 ~(4~ ( 4 c í ox í ~ bu í ~2. ~î n í l~ox i4-bens:!] 4- ion í 1)-6 - (hí drox í ~.n ΐ eii í )-tet-mhidro-2H-pirán-3,4,5-trioî; (2S,3R,4l^3S,6R)~2-(4~klór334~i2-(cikk>pc<mil-oxO-etöxi)-be^xÍlpienil)--6-(hidroxí-'m&amp;tll)'-;M·“ r així d r o - 21 ϊ "pí rán~ 3 s 5 - ír Lo I ; í2S3R?41l3S3R}”2'-(44clór-'3-(4-'(3Hdklöprí^íl-'prop-2-'inil'OXÍ)43enxil)-'fetiil)»6"(hidroxl~nie·' UÍ)4eö^i<ko-2H-piráö-3.>4s5~tóo:l; (2S,3R3R3S>bR}-2~(4-klór--3-C4~(2~(dl:Í»r--metoxi)-etil|^tenxii)->É®dl}'-d-|bídroxi-metíl)4®t« fdhidro-2H“pirán-33s5“tóol; (2S3iMR3S»6R)“2-{4~klór-3-(4-(2~cikloprüpoxi~etoxi}-benxüj~íém].V6~(hldrüxRmeÍlAíen rahidro-2H-pirán~3,4>5~triol; (2S,3R*4R,5S,6R>2>(4-k}ór“3-(4-(2“(2,2.2,-{rifl«or-etoxíVeu)xi)-ber(zíl}-fenil}~6~(biciroxkmfi' ti I)~tetrahiäro« 2H ~pi rán-3,43 -trio 1 ; és {2S3R,dR3S.6R)"2«(4-kl0r“3"(4“((E)--3~cjk!opropü-allil"Oxl)-b©nzil )-fenii)-6“{hidroxi»m«t!î)* ''ietrahidro'2í-í-piráiv-33k5“trk>]. ami no sav komplexe. 9, :&amp;z igénypontok bármelyiké szerinti eljárás» áhél a prolin és fenil-alanin alkotta csoportból választjuk, 10. A 9. igénypont szerinti eljárás, ahol az aminosav prolin és n értéke 2. !L Az 1-8. igénypoM€É:.|fc^Íylfee. :spgriiti: eljárás» ahol az 1A képlett! komplex; izotóppal jelölt. 12. A :(z531Äi4Ä,55,ri/0'-2-(4-kl0r-3»(4”(2-'cik{opropoxi'-etoxi)'-benzii)~fenil)~6~ 3(M#^K!-îElÂ)4é«t«ôi^te4Â#»n-3,43-tôo| - bisz(X-proîin} komplex kristályos alakja, azzal jellemezvén hogy a pör40ntg®dífírakeiős mintázata 4.08, 17,IP és 21,12 2Θ fokoknál (± 0,05 20 fok) csúcsokat tartalmaz, ahol a por-rüntgendiffrakcíós mintázat CuK«i sugárzás segítségé-vél készüli. 13. À 12, Igénypont szerinti kristályos alak, azzal jellemezve, hegy (1) a por-römgendíifrakciós mintázata 4,08* 6,04,17,19) 19,86 és 21,12 20 fokoknál (± 0,03 20 fok) csúcsokat tartalmaz; vagy (íí) a poMöntgendifírakciós mintázata 4,08, 6,04, 14,23, 16,45, 17,19» 17,89, 19,86, 20,61 és 21.12 20 fokoknál (± 0,05 29 fok) csúcsokat tanai máz. 14. A 12, igénypont szerinti kristályos alak, 1M&amp;! jeíIe$S|p% hogy a pop -röntgendiffrakciós mintázata 4,08. 6,04, 7,50. 9,88, 12,31, 14,23, 16,45, 17,19, 17,89. 18,47, 18,97, 19,86,20,61 és 21,12 2Θ tokoknál (± 0,05 20 fok.) csúcsokat tartalmim, 'S . .·' a .< f iv.ví. •íiv Ä f^J.Si-#i?,5Siö7i>-2^(4“klör“3-{4“(2-ciklopropoxi^etosi)“benzii)-feiiil)"-6-“(h:ídf0ki^öic4.íI}~u4mhídK>“2f/'pirán--3.4;.5~irioI - bisz{X~prolin) komplex kristályos alakja, azzal j«íléMe&amp;ve* hogy olvadáspontja körülbelül 15PC £ 1°C, differenciál pásztázd kalorimetriáv&amp;í meghatározva lO°C/perc sebességgel 5Ö°€-ról 200°C-ra melegítve.
HUE09808859A 2008-08-22 2009-08-21 Eljárás SGLT2 inhibitorok elõállítására HUE029970T2 (hu)

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