HRP20151416T1 - Postupak pripreme /(3-hidroksipiridin-2-karbonil)amino//alkanskih kiselina, estera i amida - Google Patents

Postupak pripreme /(3-hidroksipiridin-2-karbonil)amino//alkanskih kiselina, estera i amida Download PDF

Info

Publication number
HRP20151416T1
HRP20151416T1 HRP20151416T HRP20151416T HRP20151416T1 HR P20151416 T1 HRP20151416 T1 HR P20151416T1 HR P20151416 T HRP20151416 T HR P20151416T HR P20151416 T HRP20151416 T HR P20151416T HR P20151416 T1 HRP20151416 T1 HR P20151416T1
Authority
HR
Croatia
Prior art keywords
acid
acids
linear
branched
heteroaryl
Prior art date
Application number
HRP20151416T
Other languages
English (en)
Inventor
Christopher M Lanthier
Boris Gorin
Jan Oudenes
Craig Edward Dixon
Alan Quigbo Lu
James Densmore Copp
John Michael Janusz
Original Assignee
Akebia Therapeutics Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Akebia Therapeutics Inc filed Critical Akebia Therapeutics Inc
Publication of HRP20151416T1 publication Critical patent/HRP20151416T1/hr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • 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
    • C07D213/60—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 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • 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
    • C07D213/60—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 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/803—Processes of preparation
    • 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
    • C07D213/60—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 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/824—Palladium

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Inorganic Chemistry (AREA)
  • Epidemiology (AREA)
  • Materials Engineering (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Ophthalmology & Optometry (AREA)
  • Cardiology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)

Claims (9)

1. Postupak pripreme spoja formule: [image] gdje A jest prsten izabran između: i) supstituiranog ili nesupstituiranog C6 ili C10 arila; ili ii) supstituiranog ili nesupstituiranog C1-C9 heteroarila; R10 predstavlja jednu ili više nezavisno izabranih po izboru prisutnih supstitucija za vodik; X se izabire između: i) -OH; ii) -OR3; iii) -NR4R5; i iv) -OM1; R3 jest C1-C12 linearni, C3-C12 razgranati ili C3-C12 ciklički alkil; C2-C12 linearni, C3-C12 razgranati ili C3-C12 ciklički alkenil; ili C2-C12 linearni, C3-C12 razgranati ili C3-C12 ciklički alkinil, ili benzil; R4 i R5 su svaki nezavisno vodik, C1-C12 linearni, C3-C12 razgranati ili C3-C12 ciklički alkil; C2-C12 linearni, C3-C12 razgranati ili C3-C12 ciklički alkenil; ili C2-C12 linearni, C3-C12 razgranati ili C3-C12 ciklički alkinil; benzil; ili R4 i R5 mogu biti uzeti zajedno s atomom dušika da formiraju 3- do 10-eročlani prsten, gdje prsten po izboru može sadržavati jedan ili više heteroatoma izabrana između kisika (O), dušika (N), ili sumpora (S); M1 je farmaceutski prikladan kation; R7a i R7b su svaki nezavisno: i) vodik; ili ii) C1-C6 linearni, C3-C6 razgranati ili C3-C6 ciklički alkil; R8 se izabire između vodika, metila, ili etila; i indeks n jest cijeli broj od 1 do 4; ili njegove farmaceutski prikladne soli, koji obuhvaća: A) reakciju boronske kiseline ili estera formule: [image] gdje Y jest OR20, R20 je vodik ili C1-C6 linearni, C3-C6 razgranati, ili C3-C6 ciklički alkil, ili dvije OR20 jedinice mogu biti uzete zajedno da formiraju 5- do 7-eročlani C3-C10 ciklički ester, s 3,5-dihalo-2-cijanopiridinom formule: [image] svaki Z je nezavisno klor ili brom, u prisutnosti katalizatora, radi formiranja 5-aril ili 5-heteroaril-3-halo-2-cijanopiridina formule: [image] B) reakciju 5-aril ili 5-heteroaril-3-halo-2-cijanopiridina formiranog u koraku (A) s alkoksid anionom formule: [image] gdje R2 jest C1-C12 linearni alkil ili C3-C12 razgranati alkil, radi formiranja 5-aril ili 5-heteroaril-3-alkoksi-2-cijanopiridina formule: [image] C) reakciju 5-aril ili 5-heteroaril-3-alkoksi-2-cijanopiridina formiranog u koraku (B) s kiselinom radi formiranja 5-aril ili 5-heteroaril-3-hidroksi-2-karboksipiridina formule: [image] i D) reakciju 5-aril ili 5-heteroaril-3-hidroksi-2-karboksipiridina formiranog u koraku (C) sa spojem formule: [image]
2. Postupak prema zahtjevu 1, gdje boronska kiselina u koraku (A) jest supstituirana ili nesupstituirana fenil boronska kiselina; i/ili gdje boronska kiselina u koraku (A) jest fenil boronska kiselina gdje R10 predstavlja jednu ili više supstitucija za vodik nezavisno izabranih između: i) C1-C12 linearni, C3-C12 razgranati, ili C3-C12 ciklički alkil, alkenil, i alkinil; ii) C6 ili C10 aril; iii) C7 ili C11 alkilenaril; iv) C1-C9 heterociklički prstenovi; v) C1-C9 heteroaril prstenovi; 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; gdje X jest halogen, indeks j jest cijeli broj od 0 do 2, j + k =3; indeks j’ jest cijeli broj od 0 do 2, j’ + k’ = 2; xvii) -(CR102aR102b)aSR101; xviii) -(CR102aR102b)aSO2R101; i xix) -(CR102aR102b)aSO3R101; gdje svaki R101 jest nezavisno vodik, supstituirani ili nesupstituirani C1-C6 linearni, C3-C6 razgranati, ili C3-C6 ciklički alkil, fenil, benzil, heterocikl, ili heteroaril; ili dvije R101 jedinice mogu biti uzete zajedno da formiraju prsten koji ima 3-7 atoma; R102a i R102b su svaki nezavisno vodik ili C1-C4 linearni ili C3-C4 razgranati alkil; indeks "a" jest od 0 do 4.
3. Postupak prema zahtjevima 1 ili 2, gdje R10 jest jedna ili više jedinica nezavisno izabranih između: i) C1-C12 linearni, C3-C12 razgranati ili C3-C12 ciklički alkil; ii) C1-C12 linearni, C3-C12 razgranati ili C3-C12 ciklički alkoksi; ili iii) halogen.
4. Postupak prema bilo kojem od zahtjeva 1 do 3, gdje se boronska kiselina u koraku (A) izabire između 2-fluorofenilboronske kiseline, 3-fluorofenilboronske kiseline, 4-fluorofenilboronske kiseline, 2-klorofenilboronske kiseline, 3-klorofenilboronske kiseline, 4-klorofenilboronske kiseline, 2-metilfenilboronske kiseline, 3-metilfenilboronske kiseline, 4-metilfenilboronske kiseline, 2-metoksifenilboronske kiseline, 3-metoksifenil-boronske kiseline, 4-metoksifenilboronske kiseline, 2-cijanofenilboronske kiseline, 3-cijano-fenilboronske kiseline, 4-cijanofenilboronske kiseline, 2-nitrofenilboronske kiseline, 3-nitro-fenilboronske kiseline, 4-nitrofenilboronske kiseline, 2-trifluorometilfenilboronske kiseline, 3-trifluorometilfenilboronske kiseline, 4-trifluorometilfenilboronske kiseline, 2-karbamoilfenilboronske kiseline, 3-karbamoilfenilboronske kiseline, 4-karbamoilfenil-boronske kiseline, 2-(pirolidin-1-karbonil)fenilboronske kiseline, 3-(pirolidin-1-karbonil)fenilboronske kiseline, 4-(pirolidin-1-karbonil)fenilboronske kiseline, 2-(ciklopropankarbonilamino)fenilboronske kiseline, 3-(ciklopropankarbonilamino)fenilboronske kiseline, i 4-(ciklopropankarbonilamino)fenilboronske kiseline.
5. Postupak prema bilo kojem od zahtjeva 1 do 4, gdje katalizator u koraku (A) jest [1,1’-bis(difenilfosfino)ferocen]dikloro-paladij(II); i/ili gdje se spoj u koraku (D) izabire između glicina, alanina, izoleucina, leucina, valina, 2-amino-2-metil-propan kiseline, 3-aminobutan kiseline, 3-amino-3-metilbutan kiseline, 3-amino-2-metilbutan kiseline, i 4-aminobutan kiseline.
6. Postupak prema bilo kojem od zahtjeva 1 do 5, gdje X jest -OR3 ili -NR4R5 koji dalje obuhvaća korak hidrolize spoja formiranog u koraku (D) radi formiranja spoja gdje X jest -OH, poželjno gdje se hidroliza provodi u prisutnosti kiselog katalizatora, ili gdje se hidroliza provodi u prisutnosti baznog katalizatora.
7. Postupak prema zahtjevu 1, gdje spoj ima formulu: [image] i gdje A jest prsten izabran između: i) supstituiranog ili nesupstituiranog C6 ili C10 arila; ili ii) supstituiranog ili nesupstituiranog C1-C9 heteroarila; R10 predstavlja jednu ili više nezavisno izabranih po izboru prisutnih supstitucija za vodik; R7a i R7b su svaki nezavisno: i) vodik; ili ii) C1-C6 linearni, C3-C6 razgranati ili C3-C6 ciklički alkil; R8 se izabire između vodika, metila, ili etila; i indeks n jest cijeli broj od 1 do 4; ili njegove farmaceutski prikladne soli, koji obuhvaća: A) reakciju boronske kiseline ili estera formule: [image] gdje Y jest OR20, R20 je vodik ili C1-C6 linearni, C3-C6 razgranati, ili C3-C6 ciklički alkil, ili dvije OR20 jedinice mogu biti uzete zajedno da formiraju 5- do 7-eročlani C3-C10 ciklički ester, s 3,5-dihalo-2-cijanopiridinom formule: [image] svaki Z je nezavisno klor ili brom, u prisutnosti katalizatora, radi formiranja 5-aril ili 5-heteroaril-3-halo-2-cijanopiridina formule: [image] B) reakciju 5-aril ili 5-heteroaril-3-halo-2-cijanopiridina formiranog u koraku (A) s alkoksid anionom formule: [image] gdje R2 jest C1-C12 linearni alkil ili C3-C12 razgranati alkil, radi formiranja 5-aril ili 5-heteroaril-3-alkoksi-2-cijanopiridina formule: [image] C) reakciju 5-aril ili 5-heteroaril-3-alkoksi-2-cijanopiridina formiranog u koraku (B) s kiselinom radi formiranja 5-aril ili 5-heteroaril-3-hidroksi-2-karboksipiridina formule: [image] i D) reakciju 5-aril ili 5-heteroaril-3-hidroksi-2-karboksipiridina formiranog u koraku (C) sa spojem formule: [image]
8. Postupak prema zahtjevu 7, gdje boronska kiselina u koraku (A) jest supstituirana ili nesupstituirana fenil boronska kiselina; i/ili gdje boronska kiselina u koraku (A) jest fenil boronska kiselina supstituirana s jednom ili više jedinica nezavisno izabranih između: i) C1-C12 linearni, C3-C12 razgranati, ili C3-C12 ciklički alkil, alkenil, i alkinil; ii) C6 ili C10 aril; iii) C7 ili C11 alkilenaril; iv) C1-C9 heterociklički prstenovi; v) C1-C9 heteroaril prstenovi; 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; gdje X jest halogen, indeks j jest cijeli broj od 0 do 2, j + k =3; indeks j’ jest cijeli broj od 0 do 2, j’ + k’ = 2; xvii) -(CR102aR102b)aSR101; xviii) -(CR102aR102b)aSO2R101. i xix) -(CR102aR102b)aSO3R101; gdje svaki R101 jest nezavisno vodik, supstituirani ili nesupstituirani C1-C6 linearni, C3-C6 razgranati, ili C3-C6 ciklički alkil, fenil, benzil, heterocikl, ili heteroaril; ili dvije R101 jedinice mogu biti uzete zajedno da formiraju prsten koji ima 3-7 atoma; R102a i R102b su svaki nezavisno vodik ili C1-C4 linearni ili C3-C4 razgranati alkil; indeks "a" jest od 0 do 4; i/ili gdje boronska kiselina u koraku (A) jest supstituirana jednom ili više jedinica nezavisno izabranih između: i) C1-C12 linearni, C3-C12 razgranati ili C3-C12 ciklički alkil; ii) C1-C12 linearni, C3-C12 razgranati ili C3-C12 ciklički alkoksi; ili iii) halogen; i/ili gdje se boronska kiselina u koraku (A) izabire između 2-fluorofenilboronske kiseline, 3-fluorofenilboronske kiseline, 4-fluorofenilboronske kiseline, 2-klorofenilboronske kiseline, 3-klorofenilboronske kiseline, 4-klorofenilboronske kiseline, 2-metilfenilboronske kiseline, 3-metilfenilboronske kiseline, 4-metilfenilboronske kiseline, 2-metoksifenilboronske kiseline, 3-metoksifenilboronske kiseline, 4-metoksifenilboronske kiseline, 2-cijanofenilboronske kiseline, 3-cijano-fenilboronske kiseline, 4-cijanofenilboronske kiseline, 2-nitrofenilboronske kiseline, 3-nitro-fenilboronske kiseline, 4-nitrofenilboronske kiseline, 2-trifluorometilfenilboronske kiseline, 3-trifluorometilfenilboronske kiseline, 4-trifluorometilfenilboronske kiseline, 2-karbamoilfenilboronske kiseline, 3-karbamoilfenilboronske kiseline, 4-karbamoilfenil-boronske kiseline, 2-(pirolidin-1-karbonil)fenilboronske kiseline, 3-(pirolidin-1-karbonil)fenilboronske kiseline, 4-(pirolidin-1-karbonil)fenilboronske kiseline, 2-(ciklopropankarbonilamino)fenilboronske kiseline, 3-(ciklopropankarbonilamino)fenilboronske kiseline, i 4-(ciklopropankarbonilamino)fenilboronske kiseline.
9. Postupak prema zahtjevima 7 ili 8, gdje katalizator u koraku (A) jest [1,1’-bis(difenilfosfino)ferocen]dikloro-paladij(II); i/ili gdje alkoksid u koraku (B) jest metoksid; i/ili gdje se amin u koraku (D) izabire između glicina, alanina, izoleucina, leucinea, valina, 2-amino-2-metil-propan kiseline, 3-aminobutan kiseline, 3-amino-3-metilbutan kiseline, 3-amino-2-metilbutan kiseline, i 4-aminobutan kiseline.
HRP20151416T 2011-06-06 2015-12-23 Postupak pripreme /(3-hidroksipiridin-2-karbonil)amino//alkanskih kiselina, estera i amida HRP20151416T1 (hr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
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
EP12796374.2A EP2718265B1 (en) 2011-06-06 2012-06-05 Process for preparing [(3-hydroxypyridine-2-carbonyl)amino]alkanoic acids, esters and amides

Publications (1)

Publication Number Publication Date
HRP20151416T1 true HRP20151416T1 (hr) 2016-03-25

Family

ID=47262177

Family Applications (4)

Application Number Title Priority Date Filing Date
HRP20211916TT HRP20211916T1 (hr) 2011-06-06 2012-06-05 Postupak pripreme [5-(3-klorofenil)-3-hidroksipiridin-2-karbonil)-amino]ocetne kiseline iz 5-((3-klorofenil)-3-klor-piridin-2-il)-nitrila, i postupak pripreme 5-((halofenil)-3-halo-piridin-2-il)-nitril derivata
HRP20151416T HRP20151416T1 (hr) 2011-06-06 2015-12-23 Postupak pripreme /(3-hidroksipiridin-2-karbonil)amino//alkanskih kiselina, estera i amida
HRP20171740TT HRP20171740T1 (hr) 2011-06-06 2017-11-13 Derivati 5-((halofenil)-3-hidroksi-piridin-2-yl-karboksilne kiseline kao posrednici za pripravu karbonilamino alkanoinskih kiselina, njihovih estera i amida
HRP20200197TT HRP20200197T1 (hr) 2011-06-06 2020-02-06 5-((halofenil)-3-halo-piridin-2-il)-nitrilni derivati kao posrednici u pripremi [(5-(halofenila)-3-hidroksipiridin-2-karbonil)-amino]derivata alkanske kiseline

Family Applications Before (1)

Application Number Title Priority Date Filing Date
HRP20211916TT HRP20211916T1 (hr) 2011-06-06 2012-06-05 Postupak pripreme [5-(3-klorofenil)-3-hidroksipiridin-2-karbonil)-amino]ocetne kiseline iz 5-((3-klorofenil)-3-klor-piridin-2-il)-nitrila, i postupak pripreme 5-((halofenil)-3-halo-piridin-2-il)-nitril derivata

Family Applications After (2)

Application Number Title Priority Date Filing Date
HRP20171740TT HRP20171740T1 (hr) 2011-06-06 2017-11-13 Derivati 5-((halofenil)-3-hidroksi-piridin-2-yl-karboksilne kiseline kao posrednici za pripravu karbonilamino alkanoinskih kiselina, njihovih estera i amida
HRP20200197TT HRP20200197T1 (hr) 2011-06-06 2020-02-06 5-((halofenil)-3-halo-piridin-2-il)-nitrilni derivati kao posrednici u pripremi [(5-(halofenila)-3-hidroksipiridin-2-karbonil)-amino]derivata alkanske kiseline

Country Status (24)

Country Link
US (6) US9145366B2 (hr)
EP (5) EP3290404B1 (hr)
JP (6) JP6290781B2 (hr)
KR (5) KR102059366B1 (hr)
CN (1) CN106518759B (hr)
AU (4) AU2012268426B2 (hr)
CA (2) CA3135440A1 (hr)
CY (4) CY1117177T1 (hr)
DK (4) DK3290404T3 (hr)
ES (4) ES2771232T3 (hr)
HK (3) HK1196616A1 (hr)
HR (4) HRP20211916T1 (hr)
HU (4) HUE048044T2 (hr)
IL (1) IL229775A (hr)
LT (3) LT3000808T (hr)
MX (2) MX347709B (hr)
NO (1) NO2686520T3 (hr)
PL (4) PL3290404T3 (hr)
PT (4) PT3683209T (hr)
RS (3) RS54517B1 (hr)
RU (2) RU2602083C2 (hr)
SI (4) SI3683209T1 (hr)
SM (1) SMT201600013B (hr)
WO (1) WO2012170377A1 (hr)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5113838B2 (ja) 2006-06-26 2013-01-09 アケビア セラピューティックス， インコーポレイテッド プロリルヒドロキシラーゼ阻害剤および使用方法
NO2686520T3 (hr) 2011-06-06 2018-03-17
SG11201509998WA (en) * 2013-06-13 2016-01-28 Akebia Therapeutics Inc Compositions and methods for treating anemia
TW201946625A (zh) * 2013-11-15 2019-12-16 美商阿克比治療有限公司 {[5-(3-氯苯基)-3-羥基吡啶-2-羰基]胺基}乙酸之固體型式，其組合物及用途
CA2959688C (en) 2014-09-02 2024-02-27 Sunshine Lake Pharma Co., Ltd. Quinolone compounds and their use to treat diseases related to hypoxia inducible factor and/or erythropoietin
WO2016118858A1 (en) 2015-01-23 2016-07-28 Akebia Therapeutics, Inc. Solid forms of 2-(5-(3-fluorophenyl)-3-hydroxypicolinamido)acetic acid, compositions, and uses thereof
EP3270922A4 (en) * 2015-03-20 2018-08-01 Akebia Therapeutics Inc. Deuterium-enriched hypoxia-inducible factor prolyl hydroxylase enzyme inhibitors
CN106146395B (zh) 2015-03-27 2019-01-01 沈阳三生制药有限责任公司 3-羟基吡啶化合物、其制备方法及其制药用途
DK3277270T3 (da) 2015-04-01 2021-12-06 Akebia Therapeutics Inc Sammensætninger og fremgangsmåder til behandling af anæmi
AU2017376517B2 (en) * 2016-12-13 2021-03-25 Crystal Pharmaceutical (Suzhou) Co., Ltd. Novel crystalline forms of {[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl] amino} acetic acid and processes for preparation thereof
AU2017406103B2 (en) * 2017-03-29 2023-12-14 Emerald Health Pharmaceuticals, Inc. Cannabidiol derivatives as inhibitors of the HIF prolyl hydroxylases activity
WO2019028150A1 (en) 2017-08-01 2019-02-07 Akebia Therapeutics, Inc. COMPOSITIONS FOR USE IN METHODS OF TREATING HEMOGLOBINOPATHIES
CN112088155A (zh) * 2018-05-09 2020-12-15 阿克比治疗有限公司 用于制备2-[[5-(3-氯苯基)-3-羟基吡啶-2-羰基]氨基]乙酸的方法
WO2020075199A1 (en) 2018-10-12 2020-04-16 Mylan Laboratories Limited Polymorphic forms of vadadustat
US11970450B2 (en) 2018-11-28 2024-04-30 Sandoz Ag Multi-component crystals of an orally available HIF prolyl hydroxylase inhibitor
US20220204451A1 (en) 2019-04-26 2022-06-30 Kaneka Corporation Method for producing a vadadustat intermediate
US11524939B2 (en) 2019-11-13 2022-12-13 Akebia Therapeutics, Inc. Solid forms of {[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino} acetic acid
CN111087343B (zh) * 2019-11-29 2022-02-18 万华化学集团股份有限公司 一种羟基吡啶配体及其制备方法和催化应用
WO2021117767A1 (ja) * 2019-12-10 2021-06-17 田辺三菱製薬株式会社 含窒素ヘテロアリールカルボキサミド酢酸誘導体の製造方法
EP4094832A4 (en) 2020-01-24 2024-04-17 Aps Japan Co Ltd PHOTOCATALYST UNIT AND MASK PROVIDED WITH A PHOTOCATALYST UNIT
US20230286918A1 (en) 2020-07-02 2023-09-14 Akebia Therapeutics, Inc. Manufacturing process for 3,5-dichloropicolinonitrile for synthesis of vadadustat
GB202011431D0 (en) * 2020-07-23 2020-09-09 Johnson Matthey Plc Polymorphs of vadadustat and methods for preparing the polymorphs
WO2023111990A1 (en) 2021-12-17 2023-06-22 Akebia Therapeutics, Inc. Selective phd1 inhibitor compounds, compositions, and methods of use

Family Cites Families (111)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3655679A (en) * 1969-06-25 1972-04-11 Merck & Co Inc Certain aryl pyridine carboxylic acid derivatives
US3703582A (en) * 1970-04-20 1972-11-21 Merck & Co Inc Aryl pyridine carboxylic acids in the treatment of inflammation
US3894920A (en) 1971-12-21 1975-07-15 Sagami Chem Res Process for preparing alkyl-substituted 3,6-dihydro-o-dioxin derivatives
US4016287A (en) 1972-07-17 1977-04-05 Boehringer Ingelheim Gmbh Dermatological compositions containing an acylamino-carboxylic acid or an alkyl ester thereof
TW219933B (hr) 1990-02-26 1994-02-01 Lilly Co Eli
US5405613A (en) 1991-12-11 1995-04-11 Creative Nutrition Canada Corp. Vitamin/mineral composition
TW352384B (en) 1992-03-24 1999-02-11 Hoechst Ag Sulfonamido- or sulfonamidocarbonylpyridine-2-carboxamides, process for their preparation and their use as pharmaceuticals
DE4219158A1 (de) 1992-06-11 1993-12-16 Thomae Gmbh Dr K Biphenylderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
DE59401923D1 (de) * 1993-11-02 1997-04-10 Hoechst Ag Substituierte heterocyclische Carbonsäureamidester, ihre Herstellung und ihre Verwendung als Arzneimittel
ES2101421T3 (es) 1993-11-02 1997-07-01 Hoechst Ag Amidas de acidos carboxilicos heterociclicos sustituidos, su preparacion y su utilizacion como medicamentos.
NZ270267A (en) 1993-12-30 1997-03-24 Hoechst Ag 3-hydroxypyridin-2yl (and -quinolin-2-yl) carboxamide derivatives and pharmaceutical compositions
DE4410480A1 (de) 1994-03-25 1995-09-28 Hoechst Ag Sulfonamidocarbonylpyridin-2-carbonsäureesteramide sowie ihre Pyridin-N-oxide, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
DE4410423A1 (de) 1994-03-25 1995-09-28 Hoechst Ag Sulfonamidocarbonylpyridin-2-carbonsäureamide sowie ihre Pyridin-N-oxide, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
US5789426A (en) 1995-01-20 1998-08-04 Cornell Research Foundation, Inc. Method for the treatment of fibroproliferative disorders by application of inhibitors of protein hydroxylation
IL135495A (en) 1995-09-28 2002-12-01 Hoechst Ag Intermediate compounds for the preparation of quinoline-converted amines - 2 - carboxylic acid
JPH09221476A (ja) 1995-12-15 1997-08-26 Otsuka Pharmaceut Co Ltd 医薬組成物
AU5762896A (en) 1996-04-30 1997-11-19 Hoechst Aktiengesellschaft 3-alkoxypyridine-2-carboxylic acid amide esters, their preparation and the ir use as drugs
DE19620041A1 (de) 1996-05-17 1998-01-29 Merck Patent Gmbh Adhäsionsrezeptor-Antagonisten
DE19650215A1 (de) 1996-12-04 1998-06-10 Hoechst Ag 3-Hydroxypyridin-2-carbonsäureamidester, ihre Herstellung und ihre Verwendung als Arzneimittel
US6277865B1 (en) 1997-06-27 2001-08-21 Aventis Pharmaceuticals Products Inc. Piperididinyl and N-amidinopiperidinyl derivatives
CN1282319A (zh) 1997-10-09 2001-01-31 小野药品工业株式会社 氨基丁酸衍生物
DE19746287A1 (de) 1997-10-20 1999-04-22 Hoechst Marion Roussel De Gmbh Substituierte Isochinolin-2-Carbonsäureamide, ihre Herstellung und ihre Verwendung als Arzneimittel
US6159379A (en) 1999-05-04 2000-12-12 Baker Hughes Incorporated Organic ammonium salts for the removal of water soluble organics in produced water
JP2001048786A (ja) 1999-08-05 2001-02-20 Yamanouchi Pharmaceut Co Ltd 三環式ヘテロアリール誘導体
US6589758B1 (en) 2000-05-19 2003-07-08 Amgen Inc. Crystal of a kinase-ligand complex and methods of use
US6849718B2 (en) 2001-03-20 2005-02-01 Dana Farber Cancer Institute, Inc. Muteins of hypoxia inducible factor alpha and methods of use thereof
US6855510B2 (en) 2001-03-20 2005-02-15 Dana Farber Cancer Institute, Inc. Pharmaceuticals and methods for treating hypoxia and screening methods therefor
AU2002241154A1 (en) 2001-03-21 2002-10-03 Isis Innovation Ltd. Assays, methods and means relating to hypoxia inducible factor (hif) hydroxylase
SE0101327D0 (sv) 2001-04-12 2001-04-12 Astrazeneca Ab New crystalline forms
US6566088B1 (en) 2001-10-04 2003-05-20 Board Of Regents, The University Of Texas System Prolyl-4-hydroxylases
GB0124941D0 (en) 2001-10-17 2001-12-05 Glaxo Group Ltd Chemical compounds
CA3094774A1 (en) 2001-12-06 2003-07-03 Fibrogen, Inc. Use of hif prolyl hydroxylase inhibitors for treating neurological disorders
EP1556033A4 (en) 2002-05-17 2006-05-31 Celgene Corp METHODS AND COMPOSITIONS USING CYTOKINE INHIBITOR SELECTIVE MEDICAMENTS FOR THE TREATMENT AND MANAGEMENT OF CANCERS AND OTHER DISEASES
EP1545538A2 (en) 2002-08-29 2005-06-29 Merck & Co., Inc. N-biarylmethyl aminocycloalkanecarboxamide derivatives
ES2337043T3 (es) 2002-10-16 2010-04-20 Isis Innovation Limited Metodos de escrutinio empleando un modelo estructural de fih.
CA2506799A1 (en) 2002-11-21 2004-06-10 Eli Lilly And Company Mixed lineage kinase modulators
US8124582B2 (en) 2002-12-06 2012-02-28 Fibrogen, Inc. Treatment of diabetes
US7618940B2 (en) 2002-12-06 2009-11-17 Fibrogen, Inc. Fat regulation
US7183287B2 (en) 2003-04-03 2007-02-27 Pharmacia Corporation Substituted pyrimidinones
US20060251638A1 (en) 2003-06-06 2006-11-09 Volkmar Guenzler-Pukall Cytoprotection through the use of hif hydroxylase inhibitors
JP2006527200A (ja) 2003-06-06 2006-11-30 ファイブロゲン インコーポレイティッド 窒素含有ヘテロアリール化合物および内因性エリトロポエチンを増加させる際のそれらの使用方法
US8614204B2 (en) 2003-06-06 2013-12-24 Fibrogen, Inc. Enhanced erythropoiesis and iron metabolism
GB0314129D0 (en) 2003-06-18 2003-07-23 Astrazeneca Ab Therapeutic agents
WO2005108370A1 (ja) 2004-04-16 2005-11-17 Ajinomoto Co., Inc. ベンゼン化合物
ATE443775T1 (de) 2004-05-28 2009-10-15 Fibrogen Inc Hif-prolylhydroxylase-aktivitätstest
JP2008500951A (ja) 2004-05-31 2008-01-17 田辺三菱製薬株式会社 二環化合物
EP1771169A1 (en) 2004-07-14 2007-04-11 PTC Therapeutics, Inc. Methods for treating hepatitis c
TW200616969A (en) 2004-09-17 2006-06-01 Tanabe Seiyaku Co Imidazole compound
WO2006084210A2 (en) 2005-02-04 2006-08-10 Regents Of The University Of California, San Diego Hif modulating compounds and methods of use thereof
DE102005019712A1 (de) 2005-04-28 2006-11-09 Bayer Healthcare Ag Dipyridyl-dihydropyrazolone und ihre Verwendung
WO2006133391A2 (en) 2005-06-06 2006-12-14 Fibrogen, Inc. Improved treatment for anemia using a hif-alpha stabilising agent
AU2006259352A1 (en) 2005-06-15 2006-12-28 Fibrogen, Inc. Use of HIF 1alfa modulators for treatment of cancer
WO2007033216A2 (en) 2005-09-12 2007-03-22 Beth Israel Deaconess Medical Center Methods and compositions for the treatment and diagnosis of diseases characterized by vascular leak, hypotension, or a procoagulant state
WO2007038571A2 (en) 2005-09-26 2007-04-05 Smithkline Beecham Corporation Prolyl hydroxylase antagonists
US20090176726A1 (en) 2005-10-11 2009-07-09 Fisher David E Methods for treating mitf-related disorders
EP1960363B1 (en) 2005-12-09 2014-01-22 Amgen, Inc. Quinolone based compounds exhibiting prolyl hydroxylase inhibitory activity, compositions and uses thereof
MX2008008608A (es) 2006-01-09 2009-03-04 Btg Int Ltd Moduladores de factor i inducible por hipoxia y usos relacionados.
WO2007082899A1 (en) 2006-01-17 2007-07-26 Vib Vzw Inhibitors of prolyl-hydroxylase 1 for the treatment of skeletal muscle degeneration
TW200738709A (en) 2006-01-19 2007-10-16 Osi Pharm Inc Fused heterobicyclic kinase inhibitors
JP4801451B2 (ja) 2006-01-19 2011-10-26 株式会社日立ハイテクノロジーズ 走査電子顕微鏡等に用いる電子銃の制御装置及び制御方法
ITMI20060179A1 (it) 2006-02-02 2007-08-03 Abiogen Pharma Spa Procedimento per la risoluzione di miscele racemiche e complesso diastereoisomerico di un agente risolvente e di unantiomero di interesse
WO2007101204A1 (en) 2006-02-27 2007-09-07 Alcon Research, Ltd. Method of treating glaucoma
TW200808793A (en) 2006-03-07 2008-02-16 Smithkline Beecham Corp Prolyl hydroxylase inhibitors
US7588924B2 (en) 2006-03-07 2009-09-15 Procter & Gamble Company Crystal of hypoxia inducible factor 1 alpha prolyl hydroxylase
JP2009537558A (ja) 2006-05-16 2009-10-29 スミスクライン・ビーチャム・コーポレイション プロリルヒドロキシラーゼ阻害剤
AR061570A1 (es) 2006-06-23 2008-09-03 Smithkline Beecham Corp Compuesto de glicina sustituido en el n heteroaromatico composicion farmaceutica que lo comprende, su uso para preparar un medicamento, procedimientos para preparar dicha composicion farmaceutica y para preparar el compuesto
JP5113838B2 (ja) 2006-06-26 2013-01-09 アケビア セラピューティックス， インコーポレイテッド プロリルヒドロキシラーゼ阻害剤および使用方法
TW200845994A (en) 2007-01-12 2008-12-01 Smithkline Beecham Corp N-substituted glycine derivatives: prolyl hydroxylase inhibitors
TW200845991A (en) 2007-01-12 2008-12-01 Smithkline Beecham Corp N-substituted glycine derivatives: hydroxylase inhibitors
EP2155680B1 (en) 2007-04-18 2013-12-04 Amgen, Inc Indanone derivatives that inhibit prolyl hydroxylase
AU2008241503A1 (en) 2007-04-18 2008-10-30 Merck Sharp & Dohme Corp. Novel 1,8-naphthyridine compounds
ES2389063T3 (es) 2007-05-04 2012-10-22 Amgen, Inc Derivados de tienopiridina y tiazolopiridina que inhiben la actividad prolil hidroxilasa
EP2160187B1 (en) 2007-05-16 2013-05-22 Merck Sharp & Dohme Corp. Spiroindalones
CN101765596B (zh) 2007-05-18 2015-04-29 拜耳知识产权有限责任公司 用于治疗过增生症状和与血管生成有关疾病的缺氧诱导因子(hif)抑制剂
CN101868251B (zh) 2007-08-06 2012-10-10 千寿制药株式会社 含有HIF-1α和HIF-2α表达抑制物质的药物
TW200908984A (en) 2007-08-07 2009-03-01 Piramal Life Sciences Ltd Pyridyl derivatives, their preparation and use
WO2009037570A2 (en) 2007-08-10 2009-03-26 Crystalgenomics, Inc. Pyridine derivatives and methods of use thereof
WO2009035534A2 (en) 2007-09-07 2009-03-19 The Cleveland Clinic Foundation Treatment of ischemic eye disease by the systematic pharmaceutical activation of hypoxia inducible factor (hif)
WO2009039321A1 (en) 2007-09-19 2009-03-26 Smithkline Beecham Corporation Prolyl hydroxylase inhibitors
WO2009039323A1 (en) 2007-09-19 2009-03-26 Smithkline Beecham Corporation Prolyl hydroxylase inhibitors
WO2009043093A1 (en) 2007-10-04 2009-04-09 Newsouth Innovations Pty Limited Hif inhibition
WO2009049112A1 (en) 2007-10-10 2009-04-16 Smithkline Beecham Corporation Prolyl hydroxylase inhibitors
WO2009067790A1 (en) 2007-11-26 2009-06-04 Uti Limited Partnership STIMULATION OF HYPOXIA INDUCIBLE FACTOR -1 ALPHA (HIF-1α) FOR THE TREATMENT OF CLOSTRIDIUM DIFFICILE ASSOCIATED DISEASE (CDAD), FOR INTESTINAL MOTILITY AND FOR DETECTING INFECTION
WO2009070644A1 (en) 2007-11-30 2009-06-04 Smithkline Beecham Corporation Prolyl hydroxylase inhibitors
JP2011508725A (ja) 2007-11-30 2011-03-17 グラクソスミスクライン・リミテッド・ライアビリティ・カンパニー プロリルヒドロキシラーゼ阻害剤
US8269008B2 (en) 2007-12-03 2012-09-18 Fibrogen, Inc. Oxazolopyridine and isoxazolopyridine derivatives for use in the treatment of HIF-mediated conditions
US20100298324A1 (en) 2007-12-19 2010-11-25 Smith Kline Beecham Corporation Prolyl Hydroxylase Inhibitors
US20110003013A1 (en) 2008-01-04 2011-01-06 Garvan Institute Of Medical Research Method of increasing metabolism
US8952160B2 (en) 2008-01-11 2015-02-10 Fibrogen, Inc. Isothiazole-pyridine derivatives as modulators of HIF (hypoxia inducible factor) activity
CA2716706C (en) * 2008-03-03 2014-02-18 Irm Llc Compounds and compositions as tlr activity modulators
US20090228298A1 (en) * 2008-03-04 2009-09-10 The General Electric Company System and method of morphology feature analysis of physiological data
EP2268143A4 (en) * 2008-03-20 2012-06-27 Forest Lab Holdings Ltd NEW PIPERIDINE DERIVATIVES AS INHIBITORS OF THE STEAROYL COA DESATURASE
AR071997A1 (es) 2008-06-04 2010-07-28 Bristol Myers Squibb Co Forma cristalina de 6-((4s)-2-metil-4-(2-naftil)-1,2,3,4-tetrahidroisoquinolin-7-il)piridazin-3-amina
BRPI0916233A2 (pt) * 2008-07-23 2018-03-13 F.Hoffman-La Roche Ag compostos heterocíclicos antivirais
AU2009290365B2 (en) 2008-09-15 2014-08-14 Kasina Laila Innova Pharmaceuticals Private Limited Anti-cancer drugs and uses relating thereto for metastatic malignant melanoma and other cancers
JP5649584B2 (ja) 2008-11-14 2015-01-07 フィブロジェン インコーポレイテッド Ｈｉｆヒドロキシラーゼ阻害剤としてのチオクロメン誘導体
BRPI1013432B1 (pt) * 2009-03-31 2019-12-17 Kissei Pharmaceutical derivado de indolizina e composição farmacêutica
CA2774039A1 (en) 2009-11-06 2011-05-12 Aerpio Therapeutics Inc. Methods for increasing the stabilization of hypoxia inducible factor-1 alpha
NO2686520T3 (hr) 2011-06-06 2018-03-17
MX2013014310A (es) * 2011-06-06 2014-01-23 Akebia Therapeutics Inc Compuestos y composiciones para estabilizar el factor-2 alfa inducible por hipoxia como un metodo para tratar el cancer.
US20130022974A1 (en) 2011-06-17 2013-01-24 The Regents Of The University Of Michigan Dna methylation profiles in cancer
JP6099644B2 (ja) 2011-07-22 2017-03-22 ベイジン ベータ ファーマシューティカルズ カンパニー， リミテッド プロリルヒドロキシラーゼ阻害剤としての化合物の多形体、およびその使用
KR20160061911A (ko) 2013-04-08 2016-06-01 데니스 엠. 브라운 최적하 투여된 화학 화합물의 치료 효과
SG11201509998WA (en) 2013-06-13 2016-01-28 Akebia Therapeutics Inc Compositions and methods for treating anemia
MX2016002014A (es) 2013-08-16 2016-07-21 Ohio State Innovation Foundation Composiciones y metodos para modular la metilacion de dna.
TW201946625A (zh) 2013-11-15 2019-12-16 美商阿克比治療有限公司 {[5-(3-氯苯基)-3-羥基吡啶-2-羰基]胺基}乙酸之固體型式，其組合物及用途
WO2015112831A1 (en) 2014-01-23 2015-07-30 Akebia Therapeutics, Inc. Compositions and methods for treating ocular diseases
WO2016118858A1 (en) 2015-01-23 2016-07-28 Akebia Therapeutics, Inc. Solid forms of 2-(5-(3-fluorophenyl)-3-hydroxypicolinamido)acetic acid, compositions, and uses thereof
EP3270922A4 (en) 2015-03-20 2018-08-01 Akebia Therapeutics Inc. Deuterium-enriched hypoxia-inducible factor prolyl hydroxylase enzyme inhibitors
DK3277270T3 (da) 2015-04-01 2021-12-06 Akebia Therapeutics Inc Sammensætninger og fremgangsmåder til behandling af anæmi
CN112088155A (zh) 2018-05-09 2020-12-15 阿克比治疗有限公司 用于制备2-[[5-(3-氯苯基)-3-羟基吡啶-2-羰基]氨基]乙酸的方法

Also Published As

Publication number Publication date
RU2016139352A (ru) 2018-12-13
NO2686520T3 (hr) 2018-03-17
KR102171315B1 (ko) 2020-10-28
JP2014522409A (ja) 2014-09-04
RS56580B1 (sr) 2018-02-28
KR102032864B1 (ko) 2019-10-16
US20210122715A1 (en) 2021-04-29
HRP20211916T1 (hr) 2022-03-18
EP3000808A1 (en) 2016-03-30
EP3683209B1 (en) 2021-11-10
CY1122639T1 (el) 2021-03-12
PL2718265T3 (pl) 2016-04-29
KR20190141805A (ko) 2019-12-24
PT3683209T (pt) 2021-12-15
HUE048044T2 (hu) 2020-05-28
JP2021059573A (ja) 2021-04-15
US20120309977A1 (en) 2012-12-06
SI3000808T1 (en) 2018-02-28
AU2012268426B2 (en) 2017-02-16
JP7039682B2 (ja) 2022-03-22
KR20190031593A (ko) 2019-03-26
AU2012268426A1 (en) 2014-01-09
EP3290404A1 (en) 2018-03-07
CA2838194A1 (en) 2012-12-13
US9776969B2 (en) 2017-10-03
JP6510094B2 (ja) 2019-05-08
US20150361043A1 (en) 2015-12-17
ES2771232T3 (es) 2020-07-06
US20190375713A1 (en) 2019-12-12
ES2559850T3 (es) 2016-02-16
RU2016139352A3 (hr) 2020-01-27
RU2013158640A (ru) 2015-07-20
MX337216B (es) 2016-02-18
HRP20200197T1 (hr) 2020-05-15
HUE057571T2 (hu) 2022-05-28
JP6816195B2 (ja) 2021-01-20
DK3683209T3 (da) 2021-12-06
DK3000808T3 (da) 2017-11-27
HUE034975T2 (en) 2018-05-02
HUE026096T2 (en) 2016-05-30
AU2017202414B2 (en) 2018-07-19
AU2020204528B2 (en) 2022-07-14
RS54517B1 (en) 2016-06-30
US20230002323A1 (en) 2023-01-05
CY1119605T1 (el) 2018-04-04
CA3135440A1 (en) 2012-12-13
SMT201600013B (it) 2016-02-25
PT2718265E (pt) 2016-02-15
KR102000485B1 (ko) 2019-07-16
KR102059366B1 (ko) 2019-12-26
PT3000808T (pt) 2017-11-23
ES2647602T3 (es) 2017-12-22
US10246416B2 (en) 2019-04-02
RU2764667C2 (ru) 2022-01-19
MX2013014228A (es) 2014-03-26
AU2018250355A1 (en) 2018-11-08
KR20140037192A (ko) 2014-03-26
CN103717575A (zh) 2014-04-09
EP2718265A4 (en) 2014-11-19
EP2718265A1 (en) 2014-04-16
CA2838194C (en) 2022-01-11
JP6290781B2 (ja) 2018-03-07
HK1216173A1 (zh) 2016-10-21
RS59902B1 (sr) 2020-03-31
US9145366B2 (en) 2015-09-29
JP7284309B2 (ja) 2023-05-30
EP3000808B1 (en) 2017-09-27
HRP20171740T1 (hr) 2018-03-09
HK1196616A1 (zh) 2014-12-19
RU2602083C2 (ru) 2016-11-10
AU2017202414A1 (en) 2017-05-04
LT3290404T (lt) 2020-02-25
ES2900572T3 (es) 2022-03-17
JP2022081597A (ja) 2022-05-31
DK3290404T3 (da) 2020-02-17
KR102293016B1 (ko) 2021-08-26
HK1252109A1 (zh) 2019-05-17
EP2718265B1 (en) 2015-12-16
US11267785B2 (en) 2022-03-08
WO2012170377A1 (en) 2012-12-13
US10738010B2 (en) 2020-08-11
IL229775A (en) 2016-06-30
EP3683209A1 (en) 2020-07-22
DK2718265T3 (en) 2016-01-25
SI2718265T1 (sl) 2016-03-31
CY1124874T1 (el) 2022-11-25
SI3290404T1 (sl) 2020-03-31
MX347709B (es) 2017-05-10
AU2018250355B2 (en) 2020-04-09
KR20190032617A (ko) 2019-03-27
PL3683209T3 (pl) 2022-02-21
JP2023103414A (ja) 2023-07-26
CY1117177T1 (el) 2017-04-05
JP2018111697A (ja) 2018-07-19
AU2020204528A1 (en) 2020-07-30
EP4026829A1 (en) 2022-07-13
KR20200121911A (ko) 2020-10-26
SI3683209T1 (sl) 2022-03-31
CN106518759A (zh) 2017-03-22
PL3290404T3 (pl) 2020-06-01
PL3000808T3 (pl) 2018-03-30
JP2019123741A (ja) 2019-07-25
PT3290404T (pt) 2020-02-19
LT3000808T (lt) 2018-01-25
US20170362178A1 (en) 2017-12-21
CN106518759B (zh) 2019-07-30
NZ618570A (en) 2015-07-31
LT3683209T (lt) 2022-01-10
EP3290404B1 (en) 2019-12-11

Similar Documents

Publication Publication Date Title
HRP20151416T1 (hr) Postupak pripreme /(3-hidroksipiridin-2-karbonil)amino//alkanskih kiselina, estera i amida
CN101580501B (zh) 3-(取代二氢异吲哚酮-2-基)-2,6-哌啶二酮的合成方法及其中间体
ES2685621T3 (es) Procesos para preparar intermedios para la fabricación de inhibidores NEP
ES2830266T3 (es) Compuestos intermedios para la preparación de sacubitril y su preparación
AR054882A1 (es) Inhibidores macrociclicos del virus de la hepatitis c
BR112014029454B1 (pt) Pirrolo [2,3-b] piridinas e métodos para prepará-los
AR055359A1 (es) Inhibidores macrociclicos del virus de la hepatitis c
EA201170096A1 (ru) Замещенные производные пиримидона
NI200900037A (es) Derivados de 2-aril-6-fenil-imidazo[1,2-alfa] piridinas, su preparación y su aplicación en terapéutica.
AR032175A1 (es) Proceso para la fabricacion de acidos n-aril-antranilicos y sus derivados
CN112920086B (zh) 一种l-酪氨酸衍生物的制备方法
MX2014000318A (es) Procedimiento de preparacion de derivados de diamida del acido antranilico sustituidos con tetrazol mediante la reaccion de acidos de pirazol con esteres antranilicos.
HRP20180976T1 (hr) Inhibitori iap
RU2015106856A (ru) Способ получения производных пиразолкарбоновой кислоты
CA2519956A1 (en) Compound
Cheng et al. Design, synthesis and preliminary evaluation of novel pyrrolidine derivatives as matrix metalloproteinase inhibitors
DE602005024623D1 (de) Neue betulinsäurederivate kondensiert im a-ring mit einer heterozyklischen gruppe
ES2555510T3 (es) Procedimiento de fabricación de salicilamidas N-sustituidas
Kökten et al. A simple, mild, and practical method for the esterification and thioesterification of anthranilic acid utilizing N-(2-Aminobenzoyl) benzotriazole
ATE501146T1 (de) Immunoinhibitorische heterocyclische verbindungen
EP3478684A1 (en) New processes for the preparation of vemurafenib
KR20100021321A (ko) Ν-페닐-2-피리미딘-아민 유도체의 제조방법
CN111961080A (zh) 氧杂螺环膦-噁唑啉配体及其制备方法和应用
ES2252894T3 (es) Procedimiento para la preparacion de 2-carbamoil piridinas.
Sabri et al. Synthesis and spectral properties of some N‐(2‐benzimidazoyl)‐α‐aminoesters and their N‐oxides