DD156120A3 - PROCESS FOR OBTAINING PROSTAGLANDINE ANALOGUE F ALTH 2 ALPHA - Google Patents

Abstract

The application of the invention relates to the recovery of prostaglandin analogues F deep 2 alpha, in which at C 15 deep is a terminal n-C deep 5- H 11 deep group, by a (CH deep 2) deep n Y. Where n can be from 0 to 6 and Y is an alkyl radical having 1 to 6 C atoms or a possibly unsupported cycloalkyl group which is substituted by one to three substituents, such as halogen atoms or hydroxyl, alkoxyl, nitro, Trihalomethyl, sulfhydryl, etc. Groups can be substituted. In some cases, Y corresponds to the OR group, where R is an aryl having six to ten C atoms or an alkyl or alkenyl having three to six atoms, that is, halogen atoms or hydroxyl, alkoxyl, nitro, trihalomethyl groups or other substituents may be substituted. At d. synthesized derivatives (II), the carboxyl group is either free or in the form of esters consisting of alkyl, alkenyl, cycloalkyl, dicycloalkyl u. Tricycloalkylalkoholen be obtained, the halogen, hydroxyl groups u.ae. be substituted. The said analogues I are obtained by the following reaction: derivatives of / 3a alpha, 4 beta, 5 alpha / hexahydro-5-hydroxy-4-substituted trans-butene-2-yl /-2H-cyclopenta (b) -furan-2 Ons are converted to the corresponding lactone by the action of a complex hydride, after which they are treated with the appropriate ylide and the protecting groups are removed.

Description

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- 14 - 2 15 2 10

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_ 215210

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MeHee πολαρηημ 3ΠΗΜβρ iopMyjiH I ^ KpMCTaJi ^ KByroT ms

TewnepaTypa πλββλθημη 113 - 115 ⁰ C. ΙΊΚ-οποκτρ

xapaKTepwcTM ^ ecKKe nojiocH norJiomeHKH npn Tax: (CHCl ₃ ) 3610, 3020, 2950, 1771, 1598, 1583, 1480, 1285, 1037, 975; (KBr) 2935, 1742, 1598, 1583, 1488, 1380, 1310, 1250, 1081, 1031, 980, 918.

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- ie - 2 15 2 10

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_ ₁₈ _ 2 15 2 10

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- 19 - 2 15 2 10

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- 83 - 2 15 2 10

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c KHTepnpeTeeKeM οπβκτροΒ.

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B 125 MJI CyXOPO βΓΙΘΤΟΗΜΤρΜ JIS. ΚΠβθΚΠ, Κ OHHyiD

κμπητητ 10 ^ aCOB 6e3 flocTyna BJiarn. Ilocjie McnapeHMH

nojiytia © T CTeKJioo6pa3HyK Maccy, KOTopaH npM saKpHCTaJiJiHsoBHBaeTCfl. ΠρΗ o6pa6oTKe MaccH xjiopo-φορΜ-3τεΗθΛ-3φκροκ: noJiy ^ aiDT 46 r (70%) TBep ^ OM φοοφοκΗβ-BOK cojiM. CTp3 ^r KTypa BeuiecTBa ^ .OKasaHa c no: 'onbx) H cneurpa.

2 15 2 10

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2 152 10

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CTpyKTypa κοτοροδ Haxo ^ MTCH β corjracjiM c S

cneKTpoB ·

Claims (4)

- 26 - 2 15 2 1 CnoeoÖ OH X - OR '', npocTarJiaB, n, MHOB / CH _{2/3 of} COX rpynna mh anKKji .kjih_ βλκθηηλ c o ^ hmm-bo Ar OMAMM yr-JiepORa MJIH I, C ΠΗΤΒϊΟ yrJiepo ^ a, κοτορΗβ, bos co ^ epsaTβ ueiiM o, n; Hy-inecTB pOKCKJIbHHX rpynn CBOOo ₁ II ₁ HHX MJIM HO, MJIM nOJIHOCTJbK) 3amMIHeHHHX B npOCTHX ΘφΜρΟΒ, CJIOHHHX 3φΜρθΒ MJIM TaJieii m / mjik saMecTMTejiM ms rpynnH raJio ΓΘΗΟΒ, TpMraJI OTeHMeTMJI, HMTpO-, - aJiKOKCK rpynnn c yrjiepo.n.a β aJiKMJibHOM η- οτ hyjis y - aTOM BOAopo.ua 215 2 10 KJiM aJiKeHMjibHan rpynna c 0 £ HKM-iiiecTbK) yrjiepo ^ a kjik u, MKJioajiKMJibHaH rpynna c TOMaMH yrJiepo.ua, bo3moeho, 3aMyHHan OflHMM-τρΘΜΗ aTOMai.'M raJioreHOB, TpKraJioreHj / .eTMJi-, ΗΜτρο-, OKCK-, wepKanTO-, aJiKOKCM rpynnaMM c oä-HKM-AByMS aTOMaM yrviepossa, ^ MaJiKMJiaMMHO rpynnaMM co ^ HMM- TpeMS aTOMawK yrJiepo ^ a β ΠΜ MJIM OR rpynna, r ^ e R - apKJibHaH rpynna c mecTbiD-flecaTb © aTOMawM KOTOpaS, BOSMOSHO, Μ03ΖΘΤ OHTb H 3aMemeHHaH niecTb © aTOMaiiiH raJioreHOB kjih rKflpoKCKJibHHMH, Ηκτρο-, TpMraJIOr 8HMeTKJI, MeplCanTOaJIKMJIbHHMK, aJIKOKCMJIbHH- MJiM, nKMeTKJiaMHHorpynnawK, coReSt pmpun. yrJiepo ^ a β ajiyifyaTiFiecKOTA ιιθπμ, hjih - aJiKMJibHas kjih aJiKeHMJibHas rpynna c Tpei / Ji-mecTbK) aTO-yrJiepo.ua, bosmoeho, 3aMeir; eHHaH raJioreHOB, rHflpoKCMJibHHMn, MepKanTorpynna-MJiM aJIKOKCHJIbHHMM rpynnaMK c ο ^ ημμ-τρθμη A - rΜαρόκοHJibHafl rpynna hjim B - BOAopoA KJiM rM ^ poKCKJibHaH rpynna, npM ^ eM, ecJiM A- -r map ο KC mi, το Β-ΒΟ, π, οροβ, MJiK, ecjiM A-BO ^ opo ^ ;, το iHMaEiH κ Men TeM, MTO Ha COe ₁ C _- KHeHKe 06-φopMyJIH II 2 j 5 2 Ί Ο η, y κΜΘβ'τ BHme npHBe # eHHoe
A rpynna OZ hjih Bossopofl,
B Bo ^ opo ^ KJiM rpynna OZ, ηρκ ^ βΜ, ecjiH A-rpynna OZ, TO B-BOβOpOfl, HJIH eCJIK A-BOflOpOfl, TO B-rpynna OZ - TpHφeHMJIMe THJIBHHM OCTaTOK, BO3MOKHO, SaiieilieHHHH Me-TOKCHJiBHOM rpynnoss MJiH o3HanaeT rpynny THna OR ⁵ ^ --- C E ⁵ γ, π, θ R. "osHa ^ aeT arrKMJi c ο, πημμ-πητβ © aTOMawM yrJiepofla, bo3MOKH0, μ 33MeCTMTeJiK H3 rpynnH ra jioreHOB, ajiKOKCHJiOB, coAepx
MH yrJiepofla β ajiHiaTK ^ ecKOH
^ osHa ^ aeT BO ^ opo ^; hjim aJiKHJiBHHe οοτετκΗ, yrJiepo ^ a, HecyoiHMH, bosmoiho, η saMecTHTejib Κ3 rpynnH raJioreHOßliJiM ajKOKCHJiOB, co ^ epKamnx O ₁ HK πητβ aTOMOB yrjiepo.ua β aJU ^ aTsraecKOM n; enK, hjih , 29 _ 2152 10 R coBMecTHO c R o6pasyK) T βλκθηηλοβημ οοτβτοκ C ^ eTBIPbMS-HIeCTbK 8, Ύ0Μ8} ΛΚ yr JiepOfla, B0 3M0KH0, ΕailiHH KHCJIOpOflHHK βΤΟΜ, HJIK 3SMeCTMTeJIK Μ3 raJIOreHOB, aJIKOKCMJIOB C OflHHM-τρβΜΗ aTO- MaMH yrjiepo / ia β βΛκφβτΗ ^ θοκοΗ η, επκ, hjih JiKH ^ cHJiKJIbHaH rpyrma c οληημ- ^ θτηρβμα H yrJiepofla β ajiKHJibHHX rpynnax, nocjie BOCCTaHOBJieHMH. jiaKTOHOBOw TpynnKpoBKK β jiaKTOJi fleii - ο6ΐΐ} βΗ φopMyJIH / CgHg / gP ^ CH / CHg / gCOX, r ^ e X BHine yKaeaHHoe sHa ^ eHHe, ποτομ OTCTpaHhKT 3 am,MTHHe rpynnH Z, npe ^ no ^ TKTeJibHO, β Βθ, π, Ηθ-opraHH ^ ecKOH cpe , n; e πρπ KaTaJiH3ej kjih nojiy ^ eHHH προ ^ κτ oömeii 6opMyjiH T X = OHj a A, B, Y κη KMeeT BHiue yKa3aHHoe 3Ha ^ eHHe, ne-B CJIOHHHH E.CnocoÖ corJiacHo nyHKTy 1, OTJiK ^ aromMHCH τε μ, ^ ίτο ^ JiH nojiyqeHHH yKaeaHHHx cjiohhhx ΘφκροΒ Ha o6m; eH <£ opMyj! RH I, r, ne X = OX, a A, B ₅ Y η η μμθβτ BHnie Hoe SHa ^ eHHe,, newcTyiOT, B, Ka3oaJiKaHOM, co ^ epxamHM οτ ojj, horo AO TJeTHpex aTOMOB yrJiepofla hjih OKcnpaHOBHM προκ3Βθ, η; ~ HHM, co, n, ep3sain; HM οτ offioro # 0 raecTH aTOMOB yrJiepo ^ a, β cpefle OecnpoTOHHoro opraHH ^ ecKoro pacTBopstTejiH. 3.Cnoco6 corJiacHO nyHKTy 1, oTJin ^ aBmMHCii TeM, nojiy ^ eniisi yKa3aHHHx cjiojekkx 3önpoB nepeso ^ HT coeoömeii q> op ^ yJiK I, r ^ e X = OH, a A, -B, Y η η μμθβτ βη-never yKasaHHoe Βκε ^ εκκθ, β cepeopsnyK) co Jib, Ha KOTOpyio οοοτΒβτοτΒ5 ^τ 3οΐΐ; ΗΜ aJiKHJiHpyBniHM peareHTOM c ο ah mm- -so- 215210 θ, τομθμμ yrjie pofla, κοτορυβ MoryT B ΙίθΠΜ OT Ο, Π, ΗΟΚ £ 0 IHeCTM ΓΜ, ΓφΟΚΟΜ JIbHHX rpynn B φ npocToro. Θφκρβ, arieTajiH mjim cjiosHoro a ^ ipa, kjim sawec-TMTejiH TaKHe, KaK raJioreH » 4.Cnoco6 corJiacHO nyHKTy 1, OTJiM ^ aBmiiMCH τθμ, * ϊτο BOCCTaHOBJieHMe JiaKTOHOBOM rpynnwpoBKM β JiaKTOJi nponpn TeMnepaType οτ O ⁰ C flo -80 C κομπλθκοηημ ₁ npejino-qTMTeJiBHO, n; MM3o6yTMJiaJiK) MorMflpMiiOM mjik