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DK2718265T3 - Fremgangsmåde til fremstilling af [(3-Hydroxypyridin-2-carbonyl)amino]alkansyrer, estere og amider - Google Patents

Fremgangsmåde til fremstilling af [(3-Hydroxypyridin-2-carbonyl)amino]alkansyrer, estere og amider Download PDF

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DK2718265T3
DK2718265T3 DK12796374.2T DK12796374T DK2718265T3 DK 2718265 T3 DK2718265 T3 DK 2718265T3 DK 12796374 T DK12796374 T DK 12796374T DK 2718265 T3 DK2718265 T3 DK 2718265T3
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linear
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heteroaryl
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Christopher M Lanthier
Boris Gorin
Jan Oudenes
Craig Edward Dixon
Alan Quigbo Lu
James Densmore Copp
John Michael Janusz
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Akebia Therapeutics Inc
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    • 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
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Claims (9)

1. Fremgangsmåde til fremstilling af en forbindelse med formlen:
hvor A er en ring valgt blandt: i) substitueret eller usubstitueret C6- eller C-i0-aryl; eller ii) substitueret eller usubstitueret C-i-Cg-heteroaryl; R10 betegner en eller flere uafhængigt valgte eventuelt foreliggende substitutioner for hydrogen; X er valgt blandt: i) -OH; ii) -OR3; iii) -NR4R5; og iv) -OM1; R3 er C1-C12 lineær, C3-C12 forgrenet eller C3-C12 cyklisk alkyl; C2-C12 lineær, C3-C12 forgrenet eller C3-C12 cyklisk alkenyl; eller C2-C12 lineær, C3-C12 forgrenet eller C3-C12 cyklisk alkynyl, eller benzyl; R4 og R5 hver især uafhængigt er hydrogen, C1-C12 lineær, C3-C12 forgrenet eller C3-C12 cyklisk alkyl; C2-C12 lineær, C3-C12 forgrenet eller C3-C12 cyklisk alkenyl; eller C2-C12 lineær, C3-C12 forgrenet eller C3-C12 cyklisk alkynyl; benzyl; eller R4 og R5 kan tages sammen med nitrogenatomet for at danne en 3-til 10-leddet ring, hvor ringen eventuelt kan indeholde en eller flere hetero-atomer valgt blandt oxygen (O), nitrogen (N) eller sulfur (S); M1 er en farmaceutisk acceptabel kation; R7a og R7b hver især uafhængigt er: i) hydrogen; eller ii) CrC6 lineær, C3-C6 forgrenet eller C3-C6 cyklisk alkyl; R8 er valgt blandt hydrogen, methyl, eller ethyl; og index n er et helt tal fra 1 til 4; eller et farmaceutisk acceptabelt salt deraf, omfattende: A) at reagere en borsyre eller ester med formlen:
hvor Y er OR20, R20 er hydrogen eller C-|-C6 lineær, C3-C6 forgrenet, eller C3-C6 cyklisk alkyl, eller to OR20 enheder kan tages sammen for at danne en 5-leddet til 7-leddet C3-Ci0 cyklisk ester, med en 3,5-dihalo-2-cyanopyridin med formlen:
hver Z uafhængigt er chlor eller brom, i nærvær af en katalysator, for at danne en 5-aryl eller 5-heteroaryl-3-halo-2-cyanopyridin med formlen:
B) at reagere 5-arylen eller 5-heteroaryl-3-halo-2-cyanopyridinen dannet i trin (A) med en alkoxidanion med formlen:
hvor R2 er C1-C12 lineær alkyl eller C3-Ci2 forgrenet alkyl, for at danne en 5-aryl eller 5-heteroaryl-3-alkoxy-2-cyanopyridin med formlen:
C) at reagere 5-arylen eller 5-heteroaryl-3-alkoxy-2-cyanopyridinen dannet i trin (B) med en syre for at danne en 5-aryl eller 5-heteroaryl-3-hydroxy-2-carboxypyridin med formlen:
og D) at reagere 5-arylen eller 5-heteroaryl-3-hydroxy-2-carboxypyridinen dannet i trin (C) med en forbindelse med formlen:
2. Fremgangsmåde ifølge krav 1, hvor borsyren i trin (A) er en substitueret eller usubstitueret phenylborsyre; og/eller hvor borsyren i trin (A) er en phenylborsyre, hvor R10 betegner en eller flere substitutioner for hydrogen uafhængigt valgt blandt: i) C1-C12 lineær, C3-C12 forgrenet, eller C3-C12 cyklisk alkyl, alkenyl og al-kynyl; ii) C6- eller C-m-aryl; iii) C7- eller Cn-alkylenaryl; iv) C1-C9 heterocykliske ringe; v) C1-C9 heteroarylringe; vi) -(CR102aR1026)aOR101, vii) -(CR102aR102b)aC(O)R101; viii) -(CR102aR102b)aC(O)OR101; ix) -(CR102aR102b)aC(O)N(R101)2; x) -(CR102aR102b)aN(R101)C(O)R101; xi) -(CR102aR102b)aN(R101)C(O)2R101; xii) -(CR102aR102b)aN(R101)2; xiii) halogen; xiv) -(CR102aR102b)i; xv) -(CR102aR102b)aNO2; xvi) -(CHjXk)aCHjXk; hvor X er halogen, index j er et helt tal fra 0 til 2, j + k = 3; index j' er et helt tal fra 0 til 2, j' + k' = 2; xvi i) -(CR102aR102b)aSR101; xviii) -(CR102aR102b)aSO2R101; og xix) -(CR102aR102b)aSO3R101; hvor hver R101 uafhængigt er hydrogen, substitueret eller usubstitueret CrC6 lineær, C3-C6 forgrenet, eller C3-C6 cyklisk alkyl, phenyl, benzyl, heterocyk-lisk, eller heteroaryl; eller to R101-enheder kan tages sammen for at danne en ring omfattende 3-7 atomer; R102a og R102b hver især uafhængigt er hydrogen eller C1-C4 lineær eller C3-C4 forgrenet alkyl; index "a" er fra 0 til 4.
3. Fremgangsmåde ifølge krav 1 eller 2, hvor R10 er en eller flere enheder valgt blandt: i) CrCi2 lineær, C3-Ci2 forgrenet eller C3-Ci2 cyklisk alkyl; ii) CrCi2 lineær, C3-Ci2 forgrenet eller C3-Ci2 cyklisk alkoxy; eller iii) halogen.
4. Fremgangsmåde ifølge et af kravene 1 til 3, hvor borsyren i trin (A) er valgt blandt 2-fluorphenylborsyre, 3-fluorphenylborsyre, 4-fluorphenylborsyre, 2-chlorphenylborsyre, 3-chlorphenylborsyre, 4-chlorphenylborsyre, 2-methyl-phenylborsyre, 3-methylphenylborsyre, 4-methylphenylborsyre, 2-methoxy-phenylborsyre, 3-methoxyphenylborsyre, 4-methoxyphenylborsyre, 2-cyano-phenylborsyre, 3-cyano-phenylborsyre, 4-cyanophenylborsyre, 2-nitrophenyl-borsyre, 3-nitro-phenylborsyre, 4-nitrophenylborsyre, 2-trifluormethylphenyl-borsyre, 3-trifluormethylphenylborsyre, 4-trifluormethylphenylborsyre, 2-car-bamoylphenylborsyre, 3-carbamoylphenylborsyre, 4-carbamoylphenyl-bor-syre, 2-(pyrrolidin-1 -carbonyl)phenylborsyre, 3-(pyrrolidin-1 -carbonyl)phenyl-borsyre, 4-(pyrrolidin-1 -carbonyl)phenylborsyre, 2-(cyclopropancarbonylami-no)phenylborsyre, 3-(cyclopropancarbonylamino)phenylborsyre og 4-(cyclo-propancarbonylamino)phenylborsyre.
5. Fremgangsmåde ifølge et af kravene 1 til 4, hvor katalysatoren i trin (A) er [1,1'-bis(diphenylphosphino)ferrocen]dichlorpalladium(ll); og/eller hvor forbindelsen fra trin (D) er valgt blandt glycin, alanin, isoleucin, leucin, valin, 2-amino-2-methyl-propansyre, 3-aminobutansyre, 3-amino-3-methylbutan-syre, 3-amino-2-methylbutansyre og 4-aminobutansyre.
6. Fremgangsmåde ifølge et af kravene 1 til 5, hvor X er -OR3 eller -NR4R5 yderligere omfattende et trin, hvor forbindelsen dannet i trin (D) hydrolyseres for at danne en forbindelse, hvor X er -OH, fortrinsvis hvor hydrolysen udføres i nærvær af en syrekatalysaor, eller hvor hydrolysen udføres i nærvær af en basekatalysator.
7. Fremgangsmåde ifølge krav 1, hvor forbindelsen har formlen:
og hvor A er en ring valgt blandt: i) substitueret eller usubstitueret C6- eller Ci0-aryl; eller ii) substitueret eller usubstitueret CrC9-heteroaryl; R10 betegner en eller flere uafhængigt valgte eventuelt foreliggende substitutioner for hydrogen; R7a og R7b hver især uafhængigt er: i) hydrogen; eller ii) CrC6 lineær, C3-C6 forgrenet eller C3-C6 cyklisk alkyl; R8 er valgt blandt hydrogen, methyl eller ethyl; og index n er et helt tal fra 1 til 4; eller et farmaceutisk acceptabelt salt deraf, omfattende: A) at reagere en borsyre eller ester med formlen:
hvor Y er OR20, R20 er hydrogen eller CrC6 lineær, C3-C6 forgrenet, eller C3- C6 cyklisk alkyl, eller to OR20-enheder kan tages sammen for at danne en 5-leddet til 7-leddet C3-C10 cyklisk ester, med en 3,5-dihalo-2-cyanopyridin med formlen:
hver Z uafhængigt er chlor eller brom, i nærvær af en katalysator, for at danne en 5-aryl eller 5-heteroaryl-3-halo-2-cyanopyridin med formlen:
B) at reagere 5-arylen eller 5-heteroaryl-3-halo-2-cyanopyridinen dannet i trin (A) med en alkoxidanion med formlen:
hvor R2 er C1-C12 lineær alkyl eller C3-C12 forgrenet alkyl, for at danne en 5-aryl eller 5-heteroaryl-3-alkoxy-2-cyanopyridin med formlen:
C) at reagere 5-arylen eller 5-heteroaryl-3-alkoxy-2-cyanopyridinen dannet i trin (B) med en syre for at danne en 5-aryl eller 5-heteroaryl-3-hydroxy-2-carboxypyridin med formlen:
og D) at reagere 5-arylen eller 5-heteroaryl-3-hydroxy-2-carboxypyridinen dannet i trin (C) med en forbindelse med formlen:
8. Fremgangsmåde ifølge krav 7, hvor borsyren i trin (A) er en substitueret eller usubstitueret phenylborsyre; og/eller hvor borsyren i trin (A) er en phenylborsyre substitueret med en eller flere enheder uafhængigt valgt blandt: i) C1-C12 lineær, C3-C12 forgrenet, eller C3-C12 cyklisk alkyl, alkenyl og al-kynyl; ii) C6- eller Ci0-aryl; iii) C7- eller Cn-alkylenaryl; iv) CrCg-heterocykliske ringe; v) Ci-C9-heteroarylringe; vi) -(CR102aR102b)aOR101; vii) -(CR102aR102b)aC(O)R101; viii) -(CR102aR102b)aC(O)OR101; ix) -(CR102aR102b)aC(O)N(R101)2; x) -(CR102aR102b)aN(R101)C(O)R101; xi) -(CR102aR102b)aN(R101)C(O)2R101; xii) -(CR102aR102b)aN(R101)2; xiii) halogen; xiv) -(CR102aR102b)i; xv) -(CR102aR102b)aNO2; xvi) -(CHj'Xk')aCHjXk; hvor X er halogen, index j er et helt tal fra 0 til 2, j + k = 3; index j' er et helt tal fra 0 til 2, j' + k' = 2; xvii) -(CR102aR102b)aSR101; xviii) -(CR102aR102b)aSO2R101; og xix) -(CR102aR102b)aSO3R101; hvor hver R101 uafhængigt er hydrogen, substitueret eller usubstitueret C1-C6 lineær, C3-C6 forgrenet, eller C3-C6 cyklisk alkyl, phenyl, benzyl, heterocyk-lisk, eller heteroaryl; eller to R101-enheder kan tages sammen for at danne en ring omfattende 3-7 atomer; R102a og R102b hver især uafhængigt er hydrogen eller C1-C4 lineær eller C3-C4 forgrenet alkyl; index "a" er fra 0 til 4; og/eller hvor borsyren i step (A) er substitueret med en eller flere enheder uafhængigt valgt blandt: i) C1-C12 lineær, C3-C12 forgrenet eller C3-C12 cyklisk alkyl; ii) C1-C12 lineær, C3-C12 forgrenet eller C3-C12 cyklisk alkoxy; eller iii) halogen; og/eller hvor borsyren i trin (A) er valgt blandt 2-fluorphenylborsyre, 3-fluorphenyl-borsyre, 4-fluorphenylborsyre, 2-chlorphenylborsyre, 3-chlorphenylborsyre, 4-chlorphenylborsyre, 2-methylphenylborsyre, 3-methylphenylborsyre, 4-me-thylphenylborsyre, 2-methoxyphenylborsyre, 3-methoxyphenylborsyre, 4-me-thoxyphenylborsyre, 2-cyanophenylborsyre, 3-cyanophenylborsyre, 4-cyano-phenylborsyre, 2-nitrophenylborsyre, 3-nitrophenylborsyre, 4-nitrophenylbor-syre, 2-trifluormethylphenylborsyre, 3-trifluormethylphenylborsyre, 4-trifluor-methylphenylborsyre, 2-carbamoylphenylborsyre, 3-carbamoylphenylborsyre, 4-carbamoylphenylborsyre, 2-(pyrrolidin-1 -carbonyl)phenylborsyre, 3-(pyrro-lidin-1 -carbonyl)phenylborsyre, 4-(pyrrolidin-1 -carbonyl)phenylborsyre, 2-(cy-clopropancarbonylamino)phenylborsyre, 3-(cyclopropancarbonylamino)phe-nylborsyre, og 4-(cyclopropancarbonylamino)phenylborsyre.
9. Fremgangsmåde ifølge krav 7 eller 8, hvor katalysatoren I trin (A) er [1,1'-bis(diphenylphosphino)ferrocen]dichlor-palladium(ll); og/eller hvor alkoxiden i trin (B) er methoxid; og/eller hvor aminosyren fra trin (D) er valgt blandt glycin, alanin, isoleucin, leucin, valin, 2-amino-2-methyl-propansyre, 3-aminobutansyre, 3-amino-3-methyl-butansyre, 3-amino-2-methylbutansyre og 4-aminobutansyre.
DK12796374.2T 2011-06-06 2012-06-05 Fremgangsmåde til fremstilling af [(3-Hydroxypyridin-2-carbonyl)amino]alkansyrer, estere og amider DK2718265T3 (da)

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US201161493536P 2011-06-06 2011-06-06
PCT/US2012/040833 WO2012170377A1 (en) 2011-06-06 2012-06-05 Process for preparing [(3-hydroxypyridine-2-carbonyl)amino]alkanoic acids, esters and amides

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DK19214405.3T DK3683209T3 (da) 2011-06-06 2012-06-05 Fremgangsmåde til fremstilling af [(5-(3-chlorphenyl)-3-hydroxypyridin-2-carbonyl)-amino]eddikesyre fra 5-((3-chlorphenyl)-3-chlor-pyridin-2-yl)-nitril og fremgangsmåde til fremstilling af 5-((halogenphenyl)-3-halogen-pyridin-2-yl)-nitrilderivater
DK17191362.7T DK3290404T3 (da) 2011-06-06 2012-06-05 5-((halophenyl)-3-halo-pyridin-2-yl)-nitrilderivater som intermediater til fremstillingen af [(5-(halophenyl)-3-hydroxypyridin-2-carbonyl)-amino]alkansyrederivater
DK12796374.2T DK2718265T3 (da) 2011-06-06 2012-06-05 Fremgangsmåde til fremstilling af [(3-Hydroxypyridin-2-carbonyl)amino]alkansyrer, estere og amider
DK15189822.8T DK3000808T3 (da) 2011-06-06 2012-06-05 5-((halophenyl)-3-hydroxy-pyridin-2-yl)-carboxylsyre-derivater som intermediater til fremstillingen af carbonylamino-alkansyrer, estere og amider deraf

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RS54517B1 (en) 2016-06-30
EP3683209A1 (en) 2020-07-22
HUE026096T2 (en) 2016-05-30
CN103717575A (zh) 2014-04-09
KR20140037192A (ko) 2014-03-26
US20210122715A1 (en) 2021-04-29
EP3000808B1 (en) 2017-09-27
EP3683209B1 (en) 2021-11-10
KR20190031593A (ko) 2019-03-26
EP3290404A1 (en) 2018-03-07
HK1252109A1 (zh) 2019-05-17
JP2018111697A (ja) 2018-07-19
MX2013014228A (es) 2014-03-26
HUE048044T2 (hu) 2020-05-28
PT2718265E (pt) 2016-02-15
ES2771232T3 (es) 2020-07-06
AU2017202414A1 (en) 2017-05-04
HUE057571T2 (hu) 2022-05-28
KR20190032617A (ko) 2019-03-27
KR102032864B1 (ko) 2019-10-16
JP6290781B2 (ja) 2018-03-07
EP2718265A4 (en) 2014-11-19
PT3290404T (pt) 2020-02-19
JP7039682B2 (ja) 2022-03-22
DK3683209T3 (da) 2021-12-06
RU2016139352A (ru) 2018-12-13
ES2647602T3 (es) 2017-12-22
US20120309977A1 (en) 2012-12-06
EP4026829A1 (en) 2022-07-13
JP2022081597A (ja) 2022-05-31
SI3683209T1 (sl) 2022-03-31
US10246416B2 (en) 2019-04-02
AU2012268426B2 (en) 2017-02-16
PT3683209T (pt) 2021-12-15
CY1117177T1 (el) 2017-04-05
KR102293016B1 (ko) 2021-08-26
SI2718265T1 (sl) 2016-03-31
CY1124874T1 (el) 2022-11-25
AU2012268426A1 (en) 2014-01-09
NO2686520T3 (da) 2018-03-17
JP6816195B2 (ja) 2021-01-20
HK1196616A1 (zh) 2014-12-19
HRP20200197T1 (hr) 2020-05-15
NZ618570A (en) 2015-07-31
LT3683209T (lt) 2022-01-10
US9776969B2 (en) 2017-10-03
CY1119605T1 (el) 2018-04-04
RU2764667C2 (ru) 2022-01-19
JP6510094B2 (ja) 2019-05-08
PL3683209T3 (pl) 2022-02-21
US20190375713A1 (en) 2019-12-12
SMT201600013B (it) 2016-02-25
JP2021059573A (ja) 2021-04-15
SI3290404T1 (sl) 2020-03-31
CA2838194C (en) 2022-01-11
AU2018250355B2 (en) 2020-04-09
RU2602083C2 (ru) 2016-11-10
US20170362178A1 (en) 2017-12-21
KR102171315B1 (ko) 2020-10-28
JP7284309B2 (ja) 2023-05-30
HK1216173A1 (zh) 2016-10-21
HUE034975T2 (en) 2018-05-02
RS56580B1 (sr) 2018-02-28
ES2900572T3 (es) 2022-03-17
CA3135440A1 (en) 2012-12-13
CA2838194A1 (en) 2012-12-13
RU2016139352A3 (da) 2020-01-27
EP2718265B1 (en) 2015-12-16
RU2013158640A (ru) 2015-07-20
CN106518759A (zh) 2017-03-22
ES2559850T3 (es) 2016-02-16
PT3000808T (pt) 2017-11-23
IL229775A (en) 2016-06-30
LT3000808T (lt) 2018-01-25

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