HRP20190540T1 - Postupak za pripremu spoja diariltiohidantoina - Google Patents

Postupak za pripremu spoja diariltiohidantoina Download PDF

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HRP20190540T1
HRP20190540T1 HRP20190540TT HRP20190540T HRP20190540T1 HR P20190540 T1 HRP20190540 T1 HR P20190540T1 HR P20190540T T HRP20190540T T HR P20190540TT HR P20190540 T HRP20190540 T HR P20190540T HR P20190540 T1 HRP20190540 T1 HR P20190540T1
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compound
formula
copper
group
organic solvent
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HRP20190540TT
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Cyril Ben HAIM
Andras Horvath
Johan Erwin Edmond Weerts
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Aragon Pharmaceuticals, Inc.
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/08—Drugs for disorders of the urinary system of the prostate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • 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
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/14—Phosphorus; Compounds thereof
    • B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J27/195—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with vanadium, niobium or tantalum
    • B01J27/198—Vanadium
    • 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/04—Mixing
    • 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
    • C07D213/61—Halogen atoms or nitro radicals
    • 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
    • C07D213/84—Nitriles
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Chemical & Material Sciences (AREA)
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  • Urology & Nephrology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
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Claims (27)

1. Postupak za pripremu spoja (X) koji obuhvaća reakciju spoja formule (XI-c), pri čemu je P amino zaštitna skupina, sa spojem (IV) pod uvjetima za nastajanje amidne veze; u prisutnosti sredstva za spajanje amida; i u prisutnosti katalizatora; u organskom otapalu; na temperaturi u rasponu od 0 °C do oko 50 °C; da se dobije odgovarajući spoj formule (XII-c); ili, reakciju spoja (IV) s fozgenom ili analogom fozgena; u prisutnosti organske baze; u aprotonskom otapalu; zatim obradu dobivenog intermedijera izocijanata (IVa), proizvoljno bez izoliranja, sa spojem formule (XI-c); u prisutnosti baze koja nije nukleofilna; na temperaturi u rasponu od oko -20 °C do oko 80 °C; da se dobije odgovarajući spoj formule (XII-c); reakciju spoja formule (XII-c) pod uvjetima za uklanjanje amino zaštite; u organskom otapalu; na temperaturi koja je veća od sobne temperature; da se dobije odgovarajući spoj (XIII); reakciju spoja (XIII) sa spojem formule (2c-1) pri čemu X je kloro, bromo, ili jodo, i W je C1-8alkoksi ili metilamino; u prisutnosti izvora bakra (0) ili soli bakra; u prisutnosti neorganske baze; u organskom otapalu; proizvoljno u prisutnosti liganda; proizvoljno u prisutnosti sredstva za redukciju; na temperaturi u rasponu od oko sobne temperature do oko 140 °C; da se dobije odgovarajući spoj formule (2c-2) pri čemu W je C1-8alkoksi (2c-2B) ili metilamino (XVII); pretvaranje spoja formule (2c-2) u spoj (X).
2. Postupak prema zahtjevu 1 naznačen time što korak (2a) nadalje obuhvaća reakciju spoja formule (XI-c), pri čemu P je amino zaštitna skupina, sa spojem (IV) pod uvjetima za nastajanje amidne veze; u prisutnosti sredstva za spajanje amida koje je izabrano iz skupine koja se sastoji od 1,1-karbonildiimidazola, T3P, EDCI, DMTMM, i EEDQ; u prisutnosti katalizatora koji je odabran iz skupine koja se sastoji iz DBU, DBN, DABCO, trietilamina, DIPEA, TBD, TMG, MTBD, NaH, KOtBu, i LiHMDS; u organskom otapalu koje je odabrano iz skupine koja se sastoji od toluena, MeTHF, THF, iPrOAc, DCM, i IPA; na temperaturi u rasponu od oko 0 °C do oko 50 °C; da se dobije odgovarajući spoj formule (XII-c).
3. Postupak prema zahtjevu 2, naznačen time što je sredstvo za spajanje amida 1,1-karbonildiimidazol i katalizator je DBU.
4. Postupak prema zahtjevu 1 naznačen time što korak (2a-1) nadalje obuhvaća reakciju spoja (IV) s fozgenom ili analogom fozgena koji je odabran iz skupine koja se sastoji od trifozgen(bis(triklorometil) karbonata) i difozgena (triklorometil kloroformijat); u prisutnosti organske baze koja je izabrana iz skupine koja se sastoji od trietilamina, etil diizopropilamina, i DABCO; u aprotonskom otapalu koje je DCM, toluen, THF, ili MeTHF; na temperaturi koja je u rasponu od oko -20 °C do oko 50 °C; da nastane intermedijer izocijanata (IVa); zatim reakciju navedenog intermedijera izocijanata (IVa) sa spojem formule (XI-c); u prisutnosti baze koja nije nukleofilna koja je odabrana iz skupine koja se sastoji od DBU, DBN, DABCO, trietilamina, TBD, TMG, i MTBD; na temperaturi u rasponu od oko -20 °C do oko 80 °C; da se dobije odgovarajući spoj formule (XII-c).
5. Postupak prema zahtjevu 1, naznačen time što korak (2c) nadalje obuhvaća reakciju spoja (XIII) sa spojem formule (2c-1) pri čemu X je kloro, bromo, ili jodo, i W je C1-8alkoksi ili metilamino; u prisutnosti ili (1) izvora bakra (0) koji je bakar u prahu ili spužvasti bakar, ili (2) soli bakra koja je odabrana iz skupine koja se sastoji iz bakrovog klorida, bakrovog jodida, bakrovog bromida, bakrovog acetata, i bakrovog bromida; u prisutnosti neorganske baze koja je odabrana iz skupine koja se sastoji od kalijevog acetata, kalijevog karbonata, cezijevog karbonata, i CsF; u organskom otapalu koje je DMF, DMA, DMSO, acetonitril, propionitril, butironitril, ili amil alkohol; sa ili bez dodavanja bakrove (I) soli koja je izabrana iz skupine koja se sastoji od bakrovog klorida, bakrovog jodida, bakrovog bromida, i bakrovog acetata; te proizvoljno u prisutnosti liganda koji je odabran iz skupine koja se sastoji od 2-acetilcikloheksanona, TMEDA, i fenantrolina; također, proizvoljno u prisutnosti sredstva za redukcije koje je natrijev askorbat ili natrijev bisulfit; na temperaturi u rasponu od oko sobne temperature do oko 140 °C; da se dobije odgovarajući spoj formule (2c-2) pri čemu W je C1-8alkoksi (2c-2B) ili metilamino (XVII).
6. Postupak prema zahtjevu 5, naznačen time što obuhvaća reakciju spoja (XIII) sa spojem formule (2c-1) u prisutnosti bakrovog bromida; u prisutnosti TMEDA; u prisutnosti kalijevog acetata; u organskom otapalu DMA; na temperaturi u rasponu od oko 80 °C do oko 140 °C.
7. Postupak prema zahtjevu 5, naznačen time što obuhvaća reakciju spoja (XIII) sa spojem formule (2c-1) u prisutnosti izvora bakra (0) koji je bakar u prahu ili spužvasti bakar; u prisutnosti kalijevog acetata ili natrijevog pivalata; u organskom otapalu DMSO; na temperaturi u rasponu od oko 0 °C do oko 80 °C.
8. Postupak prema zahtjevu 5, naznačen time što obuhvaća reakciju spoja (XIII) sa spojem formule (2c-1) u prisutnosti izvora bakra (0) koji je bakar u prahu ili spužvasti bakar; u prisutnosti kalijevog acetata; uz dodavanje bakrove (I) soli koja je odabrana iz skupine koja se sastoji od bakrovog klorida, bakrovog jodida, bakrovog bromida, i bakrovog acetata; u organskom otapalu DMSO; na temperaturi u rasponu od oko 0 °C do oko 80 °C.
9. Postupak prema zahtjevu 1, naznačen time što korak (2d) nadalje obuhvaća pretvaranje spoja (XVII) u spoj (X) pomoću reakcije spoja (XVII) s izvorom tiokarbonila; u prisutnosti sredstva za aktiviranje; u organskom otapalu; proizvoljno u prisutnosti organske baze; na temperaturi u rasponu od oko -20 °C do oko 100 °C; da se dobije odgovarajući spoj (X).
10. Postupak prema zahtjevu 9, naznačen time što korak (2e) nadalje obuhvaća reakciju spoja (XVII) s izvorom tiokarbonila koji je odabran iz skupine koja se sastoji od O,O’-di(piridin-2-il)karbonotioata, 1,1’-tiokarbonilbis(piridin-2(1H)-ona), di(1H-imidazol-1-il)metantiona, tiofozgena, fenil tionokloroformijata, O-(2-naftil) tionokloroformijata, tolil tionokloroformijata, i tiokarbonil bis(benzotriazola); u prisutnosti sredstva za aktiviranje koje je odabrano iz skupine koja se sastoji od DMAP, NaH, i NaOH; i u organskom otapalu koje je odabrano iz skupine koja se sastoji od DMA, DMF, toluena, DMSO, ACN, THF, DCM, EtOAc, acetona, MEK, i dioksana; proizvoljno u prisutnosti organske baze koja je odabrana od trietilamina ili DIPEA; na temperaturi u rasponu od oko -20 °C do oko 100 °C; da se dobije odgovarajući spoj (X).
11. Postupak prema zahtjevu 10, naznačen time što je izvor tiokarbonila 1,1’-tiokarbonilbis(piridin-2(1H)-on).
12. Postupak prema zahtjevu 11, naznačen time što je sredstvo za aktiviranje DMAP.
13. Postupak prema zahtjevu 12, naznačen time što je organsko otapalo DMA.
14. Postupak prema zahtjevu 10, naznačen time što je izvor tiokarbonila fenil tionokloroformijat; sredstvo za aktiviranje je DMAP; organska baza je trietilamin ili DIPEA; organsko otapalo je DMA; na temperaturi u rasponu od oko - 20 °C do oko 80 °C.
15. Postupak prema zahtjevu 10, naznačen time što je izvor tiokarbonila fenil tionokloroformijat; sredstvo za aktiviranje je DMAP; organska baza je trietilamin ili DIPEA; organsko otapalo je aceton ili etil acetat; na temperaturi u rasponu od oko -20 °C do oko 80 °C.
16. Postupak prema zahtjevu 15, naznačen time što se odmah nakon ciklizacije dodaje DMAPA.
17. Postupak prema zahtjevu 10, naznačen time što korak (2e) nadalje obuhvaća reakciju fenil tionokloroformijata s DMAP da nastane kvaternarna sol koja se može izolirati, spoj (S1), zatim, reakciju spoja (XVII) sa spojem S1; u prisutnosti organske baze koja je izabrana iz trietilamina ili DIPEA; u DMA; na temperaturi u rasponu od oko -20 °C do oko 80 °C; da se dobije odgovarajući spoj (X).
18. Postupak prema zahtjevu 1, naznačen time što korak (2d) nadalje obuhvaća pretvaranje spoja formule (2c-2B) u spoj formule (2e), reakcijom spoja formule (2c-2B) s izvorom tiokarbonila; u prisutnosti sredstva za aktiviranje; u organskom otapalu; na temperaturi u rasponu od oko -20 °C do oko 100 °C; da se dobije odgovarajući spoj formule (2e); zatim, tretiranje spoja formule (2e) s metilaminom; u organskom otapalu; na približno sobnoj temperaturi; da se dobije odgovarajući spoj (X).
19. Postupak prema zahtjevu 18, naznačen time što nadalje obuhvaća reakciju spoja formule (2c-2B) s izvorom tiokarbonila koji je odabran iz skupine koja se sastoji od O,O’-di(piridin-2-il)karbonotioata, 1,1’-tiokarbonilbis(piridin-2(1H)-ona), di(1H-imidazol-1-il)metantiona, tiofozgena, fenil tionokloroformijata, O-(2-naftil) tionokloroformijata, tolil tionokloroformijata, i tiokarbonil bis(benzotriazola); u prisutnosti sredstva za aktiviranje koje je izabrano iz skupine koja se sastoji od DMAP, NaH, i NaOH; u organskom otapalu koje je odabrano iz skupine koja se sastoji od dimetilacetamida, DMF, toluena, DMSO, THF, i dioksana; na temperaturi u rasponu od oko -20 °C do oko 100 °C; da se dobije odgovarajući spoj formule (2e); zatim obradu spoja formule (2e) s metilaminom; u organskom otapalu koje je odabrano iz skupine koja se sastoji od THF, DMF, DMA, etanola, i njihove smjese u vodi; na približno sobnoj temperaturi; da se dobije odgovarajući spoj (X).
20. Postupak prema zahtjevu 19, naznačen time što obrada spoja formule (2e) s metilaminom nadalje obuhvaća upotrebu etanola kao organskog otapala.
21. Postupak prema zahtjevu 19, naznačen time što nadalje sadrži reakciju spoja formule (2c-2B) pri čemu izvor tiokarbonila je fenil tionokloroformijat; sredstvo za aktiviranje je DMAP; organsko otapalo je aceton ili etil acetat; na temperaturi u rasponu od oko -20 °C do 40 °C; da se dobije odgovarajući spoj formule (2e); zatim tretiranje spoja formule (2e) s metilaminom; u etanolu; na približno sobnoj temperaturi; da se dobije odgovarajući spoj (X).
22. Postupak prema zahtjevu 18, naznačen time što korak (2f) nadalje obuhvaća reakciju fenil tionokloroformijata s DMAP da nastane kvaternarna sol koja se može izolirati, spoj (S1), zatim, reakciju spoja (2c-2B) sa spojem S1; u prisutnosti organske baze koja je odabrana od trietilamina DIPEA; u DMA; na temperaturi u rasponu od oko -20 °C do oko 80 °C; da se dobije odgovarajući spoj (X).
23. Spoj formule (XII-c), koji se koristi za dobivanje spoja (X), pri čemu P je zaštitna amino skupina
24. Spoj prema zahtjevu 23 naznačen time što P je t-butoksikarbonil.
25. Spoj (XIII) naznačen time što se koristi za pripremu spoja (X).
26. Spoj (XVII) naznačen time što se koristi za pripremu spoja (X).
27. Spoj formule (2c-2B) naznačen time što se koristi za pripremu spoja (X).
HRP20190540TT 2014-12-19 2019-03-19 Postupak za pripremu spoja diariltiohidantoina HRP20190540T1 (hr)

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US201462094436P 2014-12-19 2014-12-19
PCT/US2015/066356 WO2016100652A2 (en) 2014-12-19 2015-12-17 Process for the preparation of a diarylthiohydantoin compound
EP15823875.8A EP3233803B1 (en) 2014-12-19 2015-12-17 Process for the preparation of a diarylthiohydantoin compound

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