HRP20221444T1 - Postupci za pripravu pi3k inhibitora - Google Patents
Postupci za pripravu pi3k inhibitora Download PDFInfo
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- HRP20221444T1 HRP20221444T1 HRP20221444TT HRP20221444T HRP20221444T1 HR P20221444 T1 HRP20221444 T1 HR P20221444T1 HR P20221444T T HRP20221444T T HR P20221444TT HR P20221444 T HRP20221444 T HR P20221444T HR P20221444 T1 HRP20221444 T1 HR P20221444T1
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- 238000000034 method Methods 0.000 title claims 24
- 239000012828 PI3K inhibitor Substances 0.000 title 1
- 229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 46
- 238000006243 chemical reaction Methods 0.000 claims 27
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 9
- 150000003512 tertiary amines Chemical class 0.000 claims 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 8
- 239000002904 solvent Substances 0.000 claims 8
- BOSVWXDDFBSSIZ-UHFFFAOYSA-N 2-(1-ethoxyethylidene)propanedinitrile Chemical compound CCOC(C)=C(C#N)C#N BOSVWXDDFBSSIZ-UHFFFAOYSA-N 0.000 claims 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- XPOLVIIHTDKJRY-UHFFFAOYSA-N acetic acid;methanimidamide Chemical compound NC=N.CC(O)=O XPOLVIIHTDKJRY-UHFFFAOYSA-N 0.000 claims 5
- -1 C1-6 alkylsulfonyl halide Chemical class 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical group CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical group CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 4
- 239000003054 catalyst Substances 0.000 claims 3
- 238000005984 hydrogenation reaction Methods 0.000 claims 3
- 239000007800 oxidant agent Substances 0.000 claims 3
- 230000003647 oxidation Effects 0.000 claims 3
- 238000007254 oxidation reaction Methods 0.000 claims 3
- DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 claims 3
- LYXHWHHENVLYCN-QMDOQEJBSA-N (1z,5z)-cycloocta-1,5-diene;rhodium;tetrafluoroborate Chemical group [Rh].F[B-](F)(F)F.C\1C\C=C/CC\C=C/1.C\1C\C=C/CC\C=C/1 LYXHWHHENVLYCN-QMDOQEJBSA-N 0.000 claims 2
- LLJITAAISCMRAR-UHFFFAOYSA-N bis[4-(trifluoromethyl)phenyl]phosphane Chemical compound C1=CC(C(F)(F)F)=CC=C1PC1=CC=C(C(F)(F)F)C=C1 LLJITAAISCMRAR-UHFFFAOYSA-N 0.000 claims 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 claims 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- 238000006646 Dess-Martin oxidation reaction Methods 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims 1
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical group C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 claims 1
- QARBMVPHQWIHKH-KHWXYDKHSA-N methanesulfonyl chloride Chemical group C[35S](Cl)(=O)=O QARBMVPHQWIHKH-KHWXYDKHSA-N 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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Claims (16)
1. Postupak, naznačen time, da obuhvaća reakciju spoja Formule XVI:
[image]
s formamidin acetatom u svrhu tvorbe spoja Formule I:
[image]
pri čemu opcionalno:
(a) navedena reakcija spoja Formule XVI s formamidin acetatom obavlja se u komponenti otapala koja sadrži 1,2-etandiol; i/ili
(b) navedena reakcija spoja Formule XVI s formamidin acetatom izvodi se na temperaturi od oko 100°C do oko 105°C; i/ili
(c) oko 8 do oko 10 ekvivalenata formamidin acetata koristi se na temelju jednog ekvivalenta spoja Formule XVI.
2. Postupak prema patentnom zahtjevu 1, naznačen time, da nadalje obuhvaća pripravu spoja Formule XVI putem postupka koji obuhvaća reakciju spoja Formule XV:
[image]
s (1-etoksietiliden)malononitrilom u prisutnosti tercijarnog amina; pri čemu opcionalno:
(a) navedeni tercijarni amin je N-metilpirolidinon; i/ili
(b) navedena reakcija spoja Formule XV s (1-etoksietiliden)malononitrilom izvodi se na otprilike sobnoj temperaturi.
3. Postupak prema patentnom zahtjevu 2, naznačen time, da nadalje obuhvaća pripravu spoja Formule XV putem postupka koji obuhvaća reakciju spoja Formule XIV-a:
[image]
s hidrazinom u prisutnosti tercijarnog amina; pri čemu P1 je C1-6 alkilsulfonil; pri čemu opcionalno:
(a) navedeni tercijarni amin je N-metilpirolidinon; i/ili
(b) navedena reakcija spoja Formule XIV-a s hidrazinom izvodi se na temperaturi od oko 35°C do oko 60°C; i/ili
(c) navedena reakcija spoja Formule XIV-a s hidrazinom obavlja se u komponenti otapala koja sadrži diklorometan; i/ili
(d) P1 je metansulfonil skupina.
4. Postupak prema patentnom zahtjevu 3, naznačen time, da nadalje obuhvaća pripravu spoja Formule XIV-a putem postupka koji obuhvaća reakciju spoja Formule XIII:
[image]
s C1-6 alkilsulfonilhalidom u prisutnosti tercijarnog amina; pri čemu opcionalno:
(a) navedeni C1-6 alkilsulfonilhalid je metansulfonil klorid; i/ili
(b) navedeni tercijarni amin je N,N-diizopropiletilamin; i/ili
(c) oko 1,1 do oko 1,5 ekvivalenata alkilsulfonilhalida koristi se na temelju jednog ekvivalenta spoja Formule XIII.
5. Postupak prema patentnom zahtjevu 4, naznačen time, da se navedena reakcija spomenutog spoja Formule XIII s C1-6 alkilsulfonilhalidom izvodi:
(a) na temperaturi od oko -10°C do oko 5°C; i/ili
(b) u komponenti otapala koja sadrži diklorometan.
6. Postupak prema bilo kojem od patentnih zahtjeva 1 do 5, naznačen time, da se sljedeći koraci: (i) reakcija navedenog spoja Formule XIII s C1-6 alkilsulfonilhalidom; (ii) reakcija navedenog spoja Formule XIV-a s hidrazinom u prisutnosti tercijarnog amina u svrhu tvorbe spoja Formule XV; i (iii) reakcija navedenog spoja Formule XV s formamidin acetatom u svrhu tvorbe spoja Formule XVI, obavljaju u istoj posudi bez izoliranja spoja Formule XIV-a ili spoja Formule XV.
7. Postupak prema patentnom zahtjevu 1, naznačen time, da nadalje obuhvaća pripravu spoja Formule XVI putem postupka koji obuhvaća reakciju soli Formule XV-a:
[image]
S (1-etoksietiliden)malononitrilom u prisutnosti tercijarnog amina, pri čemu TsOH je p-toluensulfonska kiselina; pri čemu opcionalno:
(a) navedeni tercijarni amin je N,N-diizopropiletilamin; i/ili
(b) navedena reakcija soli Formule XV-a s (1-etoksietiliden)malononitrilom izvodi se na otprilike sobnoj temperaturi; i/ili
(c) oko 1,3 do oko 1,6 ekvivalenata (1-etoksietiliden)malononitrila koristi se na temelju jednog ekvivalenta soli Formule XV-a; i/ili
(d) navedena reakcija soli Formule XV-a s (1-etoksietiliden)malononitrilom obavlja se u komponenti otapala koja sadrži etanol.
8. Postupak prema patentnom zahtjevu 7, naznačen time, da nadalje obuhvaća pripravu soli Formule XV-a putem postupka koji obuhvaća reakciju spoja Formule XXI:
[image]
s p-toluensulfonskom kiselinom, pri čemu Boc je terc-butoksikarbonil; pri čemu opcionalno:
(a) spomenuta p-toluensulfonska kiselina je monohidrat p-toluensulfonske kiseline; i/ili
(b) oko 1,3 do oko 1,6 ekvivalenata p-toluensulfonske kiseline koristi se na temelju jednog ekvivalenta spoja Formule XXI; i/ili
(c) navedena reakcija spomenutog spoja Formule XXI s p-toluensulfonskom kiselinom izvodi se na temperaturi od oko 45°C do oko 65°C; i/ili
(d) navedena reakcija spomenutog spoja Formule XXI s p-toluensulfonskom kiselinom obavlja se u komponenti otapala koja sadrži etanol.
9. Postupak prema patentnom zahtjevu 8, naznačen time, da se sljedeći koraci: (i) reakcija navedenog spoja Formule XXI s p-toluensulfonskom kiselinom u svrhu tvorbe soli Formule XV-a; i (ii) reakcija navedene soli Formule XV-a s (1-etoksietiliden)malononitrilom, obavljaju u istoj posudi bez izoliranja soli Formule XV-a.
10. Postupak prema bilo kojem od patentnih zahtjeva 8 do 9, naznačen time, da nadalje obuhvaća pripravu spoja Formule XXI, putem postupka koji obuhvaća reakciju spoja Formule XX:
[image]
s vodikovim plinom u prisutnosti jednog ili više neovisno odabranih hidrogenacijskih katalizatora, pri čemu Boc je t-butoksikarbonil.
11. Postupak prema patentnom zahtjevu 10, naznačen time, da se navedena reakcija spoja Formule XX s vodikovim plinom izvodi u prisutnosti dva neovisno odabrana hidrogenacijska katalizatora; pri čemu opcionalno jedan hidrogenacijski katalizator je bis(1,5-ciklooktadien)rodij(I)tetrafluoroborat, a drugi je (R)-(-)-1-{(S)-2-[bis(4-trifluorometilfenil)fosfin]ferocenil}etil-di-t-butilfosfin.
12. Postupak prema patentnom zahtjevu 11, naznačen time, da:
(a) oko 13,5 do oko 14,5 ekvivalenata spoja Formule XX koristi se na temelju jednog ekvivalenta od bis(1,5-ciklooktadien)rodij(I)tetrafluoroborata; i/ili
(b) oko 12 do oko 13 ekvivalenata spoja Formule XX koristi se na temelju jednog ekvivalenta od (R)-(-)-1-{(S)-2-[bis(4-trifluorometilfenil)fosfin]ferocenil}etil-di-t-butilfosfina.
13. Postupak prema bilo kojem od patentnih zahtjeva 10 do 12, naznačen time, da se spomenuta reakcija spoja Formule XX s vodikovim plinom izvodi na otprilike sobnoj temperaturi; i/ili spomenuta reakcija spoja Formule XX s vodikovim plinom obavlja u komponenti otapala koja sadrži metanol.
14. Postupak prema bilo kojem od patentnih zahtjeva 10 do 13, naznačen time, da nadalje obuhvaća pripravu spoja Formule XX putem postupka koji obuhvaća reakciju spoja Formule XIX:
[image]
s t-butil karbazatom; pri čemu opcionalno:
(a) navedena reakcija spoja Formule XIX s t-butil karbazatom izvodi se na temperaturi od oko 60°C do oko 70°C; i/ili
(b) navedena reakcija spoja Formule XIX s t-butil karbazatom obavlja se u komponenti otapala koja sadrži metanol.
15. Postupak prema patentnom zahtjevu 14, naznačen time, da nadalje obuhvaća pripravu spoja Formule XIX putem postupka koji obuhvaća oksidaciju spoja Formule XIII-a:
[image]
u prisutnosti oksidacijskog sredstva; pri čemu opcionalno:
(a) spomenuto oksidacijsko sredstvo je Dess-Martin periodinan; i/ili
(b) oko 1,2 do oko 1,7 ekvivalenata spomenutog oksidacijskog sredstva koristi se na temelju jednog ekvivalenta od spoja Formule XIII-a; i/ili
(c) spomenuta oksidacija spoja Formule XIII-a izvodi se na otprilike sobnoj temperaturi; i/ili
(d) spomenuta oksidacija spoja Formule XIII-a obavlja se u komponenti otapala koja sadrži diklorometan.
16. Spoj, naznačen time, da se bira od sljedećih:
(a) Formula XIV:
[image]
ili njegova farmaceutski prihvatljiva sol; ili
(b) Formula XV:
[image]
ili njegova farmaceutski prihvatljiva sol; ili
(c) Formula XVI:
[image]
ili njegova farmaceutski prihvatljiva sol; ili
(d) Formula XX:
[image]
ili njegova farmaceutski prihvatljiva sol; ili
(e) Formula XXI:
[image]
ili njegova farmaceutski prihvatljiva sol.
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