DK2861583T3 - Fremgangsmåde til fremstilling af hydroxylerede cyclopentylpyrimidinforbindelser - Google Patents

Fremgangsmåde til fremstilling af hydroxylerede cyclopentylpyrimidinforbindelser Download PDF

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Publication number
DK2861583T3
DK2861583T3 DK13725533.7T DK13725533T DK2861583T3 DK 2861583 T3 DK2861583 T3 DK 2861583T3 DK 13725533 T DK13725533 T DK 13725533T DK 2861583 T3 DK2861583 T3 DK 2861583T3
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DK
Denmark
Prior art keywords
formula
compound
salt
methyl
certain embodiments
Prior art date
Application number
DK13725533.7T
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English (en)
Inventor
Jonathan W Lane
Travis Remarchuk
Sagar Shakya
Keith L Spencer
Peter J Stengel
Original Assignee
Array Biopharma Inc
Genentech Inc
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Publication date
Application filed by Array Biopharma Inc, Genentech Inc filed Critical Array Biopharma Inc
Application granted granted Critical
Publication of DK2861583T3 publication Critical patent/DK2861583T3/da

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/30—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Claims (15)

1. Fremgangsmåde, som omfatter kontaktering af en forbindelse med formel IV eller et salt deraf:
hvor R1 er hydrogen eller en aminobeskyttelsesgruppe; R2 er hydrogen eller eventuelt substitueret C1-C12 alkyl; og R3 er halogen, med carbonmonoxid, carbonyleringskatalysator og alkohol med formel R4OH for at danne en forbindelse med formel III eller et salt deraf:
hvor R4 er CrC6 alkyl.
2. Fremgangsmåde ifølge krav 1, hvorved carbonyleringskatalysatoren omfatter Pd(OAc)2.
3. Fremgangsmåde ifølge krav 1-2, hvorved R1 er en Boc-gruppe.
4. Fremgangsmåde ifølge krav 1-3, hvorved R2 er methyl eller benzyl.
5. Fremgangsmåde ifølge krav 1-4, hvorved R3 er Cl.
6. Fremgangsmåde ifølge krav 1-5, hvorved R4 er isopropyl.
7. Fremgangsmåde ifølge krav 1-6, yderligere omfattende (i) at omsætte en forbindelse med formel III eller et salt deraf med en base for at danne et mellemprodukt; og (ii) at decarboxylere mellemproduktet for at fremstille en forbindelse med formel II eller et salt deraf:
8. Fremgangsmåde ifølge krav 7, hvorved basen omfatter et kalium f-butoxid.
9. Fremgangsmåde ifølge krav 7 eller 8, hvorved decarboxylering yderligere omfatter en katalysator, som omfatter Pd og hydrogengas.
10. Fremgangsmåde ifølge krav 7-9, yderligere omfattende reduktion af en forbindelse med formel II eller et salt deraf for at danne en forbindelse med formel I eller et salt deraf:
11. Fremgangsmåde ifølge krav 10, hvorved reduktionen omfatter en katalysator, som omfatter ruthenium og hydrogengas.
12. Fremgangsmåde ifølge krav 1-11, yderligere omfattende kontaktering af en forbindelse med formel XIII eller et salt deraf:
med en forbindelse
for at danne forbindelsen med formel IVa eller et salt deraf:
13. Fremgangsmåde ifølge krav 12, yderligere omfattende klorering af en forbindelse med formel XII eller et salt deraf:
for at danne forbindelsen med formel XIII eller et salt deraf.
14. Fremgangsmåde ifølge krav 13, yderligere omfattende at omsætte en forbindelse med formel X eller et salt deraf:
hvor Ra og Rb uafhængigt er C-m2 alkyl med formamidin for at danne forbindelsen med formel XII eller et salt deraf.
15. Fremgangsmåde ifølge krav 14, omfattende kontaktering af en forbindelse med formel XI:
med en lipase for at danne forbindelsen med formel X eller et salt deraf.
DK13725533.7T 2012-05-17 2013-05-17 Fremgangsmåde til fremstilling af hydroxylerede cyclopentylpyrimidinforbindelser DK2861583T3 (da)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201261648421P 2012-05-17 2012-05-17
US201361785281P 2013-03-14 2013-03-14
PCT/US2013/041624 WO2013173736A1 (en) 2012-05-17 2013-05-17 Process for making hydroxylated cyclopentylpyrimidine compounds

Publications (1)

Publication Number Publication Date
DK2861583T3 true DK2861583T3 (da) 2016-10-03

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ID=48534507

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DK13725533.7T DK2861583T3 (da) 2012-05-17 2013-05-17 Fremgangsmåde til fremstilling af hydroxylerede cyclopentylpyrimidinforbindelser

Country Status (19)

Country Link
US (1) US9309204B2 (da)
EP (1) EP2861583B1 (da)
JP (1) JP6214636B2 (da)
KR (1) KR20150020211A (da)
CN (1) CN104487430B (da)
AU (1) AU2013262568B2 (da)
BR (1) BR112014028570A2 (da)
CA (1) CA2873653A1 (da)
DK (1) DK2861583T3 (da)
ES (1) ES2588878T3 (da)
HK (1) HK1208673A1 (da)
IL (1) IL235714A0 (da)
MA (1) MA37649B1 (da)
MX (1) MX2014013865A (da)
PL (1) PL2861583T3 (da)
RU (1) RU2014151017A (da)
SG (1) SG11201407613RA (da)
SI (1) SI2861583T1 (da)
WO (1) WO2013173736A1 (da)

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KR102067850B1 (ko) 2012-05-17 2020-01-17 어레이 바이오파마 인크. 하이드록실화 사이클로펜틸피리미딘 화합물 제조 방법
MY171538A (en) 2012-05-17 2019-10-17 Genentech Inc Process for making amino compounds
MA37647A1 (fr) 2012-05-17 2016-03-31 Genentech Inc Procédé de fabrication de composés de cyclopentapyrimidine hydroxylée et sels de ceux-ci
MX353041B (es) 2012-05-17 2017-12-18 Genentech Inc Formas y formulaciones de un compuesto de pirimidinilciclopentano, composiciones y métodos de este.
MX2020009462A (es) 2013-11-15 2021-08-31 Hoffmann La Roche Procesos para la preparación de compuestos de pirimidinilciclopentano.
EP3074394B1 (en) * 2013-11-27 2019-02-20 Sunshine Lake Pharma Co., Ltd. Processes for preparing dihydropyrimidine derivatives and intermediates thereof
CN112062727B (zh) 2014-09-26 2023-10-31 豪夫迈·罗氏有限公司 用于制备(环戊并[d]嘧啶-4-基)哌嗪化合物的方法
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Also Published As

Publication number Publication date
WO2013173736A1 (en) 2013-11-21
AU2013262568A1 (en) 2015-01-22
ES2588878T3 (es) 2016-11-07
SI2861583T1 (sl) 2016-10-28
US9309204B2 (en) 2016-04-12
EP2861583B1 (en) 2016-06-29
HK1208673A1 (en) 2016-03-11
JP2015518837A (ja) 2015-07-06
IL235714A0 (en) 2015-02-01
JP6214636B2 (ja) 2017-10-18
AU2013262568B2 (en) 2017-08-31
US20150099881A1 (en) 2015-04-09
RU2014151017A (ru) 2016-07-10
CN104487430B (zh) 2016-08-24
KR20150020211A (ko) 2015-02-25
EP2861583A1 (en) 2015-04-22
SG11201407613RA (en) 2015-01-29
MA37649A1 (fr) 2016-06-30
BR112014028570A2 (pt) 2018-04-24
CA2873653A1 (en) 2013-11-21
MA37649B1 (fr) 2017-03-31
MX2014013865A (es) 2015-05-07
PL2861583T3 (pl) 2016-12-30
CN104487430A (zh) 2015-04-01

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