HRP20161209T1 - Spoj kinolona i farmaceutski pripravak - Google Patents

Spoj kinolona i farmaceutski pripravak Download PDF

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Publication number
HRP20161209T1
HRP20161209T1 HRP20161209TT HRP20161209T HRP20161209T1 HR P20161209 T1 HRP20161209 T1 HR P20161209T1 HR P20161209T T HRP20161209T T HR P20161209TT HR P20161209 T HRP20161209 T HR P20161209T HR P20161209 T1 HRP20161209 T1 HR P20161209T1
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Croatia
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alkyl
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optionally
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alkoxy
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HRP20161209TT
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English (en)
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Kenji Otsubo
Takahito Yamauchi
Yuji Ochi
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Otsuka Pharmaceutical Co., Ltd.
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Publication of HRP20161209T1 publication Critical patent/HRP20161209T1/hr

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    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
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    • 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
    • A61K31/47—Quinolines; Isoquinolines
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Claims (10)

1. Spoj kinolona prikazan s općom formulom (1): [image] ili njegova sol , naznačen time da R1 predstavlja: (3) halogen-supstituiran C1-C6 alkil, (4) C2-C6 alkenil, (5) C1-C6 alkanoil, (6) halogen-supstituiran C1-C6 alkanoil, (7) hidroksi C1-C6 alkil, (8) fenil C1-C6 alkoksi C1-C6 alkil, (9) hidroksi C1-C6 alkanoil, (10) fenil C1-C6 alkoksi C1-C6 alkanoil, (11) C1-C6 alkiltio C1-C6 alkil, (12) amino C1-C6 alkiltio C1-C6 alkil koji proizvoljno ima jednu ili dvije C1-C6 alkil skupine, (13) hidroksi C1-C6 alkiltio C1-C6 alkil, (14) karboksi C1-C6 alkiltio C1-C6 alkil, (15) C1-C6 alkoksikarbonil C1-C6 alkiltio C1-C6 alkil, (16) amino C1-C6 alkiltiokarbonil C1-C6 alkil koji proizvoljno ima jednu ili dvije C1-C6 alkil skupine, (17) hidroksi C1-C6 alkilsulfonil C1-C6 alkil, (18) karboksi C1-C6 alkilsulfonil C1-C6 alkil, (19) C1-C6 alkoksikarbonil C1-C6 alkilsulfonil C1-C6 alkil, (20) C1-C6 alkanoil C1-C6 alkilsulfonil C1-C6 alkil, (21) piperazinil C1-C6 alkilsulfonil C1-C6 alkil koji proizvoljno ima jednu C1-C6 alkil skupinu na piperazinskom prstenu, (22) piperazinilkarbonil C1-C6 alkilsulfonil C1-C6 alkil koji proizvoljno ima jednu C1-C6 alkil skupinu na piperazinskom prstenu, (23) C1-C6 alkanoil C1-C6 alkil, (24) karboksi C1-C6 alkil, (25) C1-C6 alkoksikarbonil C1-C6 alkil, (26) piperazinil C1-C6 alkoksikarbonil C1-C6 alkil koji proizvoljno ima jednu C1-C6 alkil skupinu na piperazinskom prstenu, (27) morfolinil C1-C6 alkil, (28) oksazepanil C1-C6 alkil, (29) amino C1-C6 alkil koji proizvoljno ima jednu ili dvije C1-C6 alkil skupine, (30) piperazil C1-C6 alkil koji proizvoljno ima, na piperazinskom prstenu, jedan supstituent odabran iz skupine koju čine C1-C6 alkil, C1-C6 alkoksi C1-C6 alkil, i piridil, (31) piperidil C1-C6 alkil koji proizvoljno ima jednu morfolinil skupinu, (32) azetidil C1-C6 alkil koji proizvoljno ima jednu hidroksi skupinu na azetidinskom prstenu, (33) izoindolinil C1-C6 alkil koji proizvoljno ima jednu ili dvije okso skupine, (34) amino C1-C6 alkanoiloksi C1-C6 alkil koji proizvoljno ima jedan ili dva supstituenta koji se biraju iz skupine koju čine C1-C6 alkil i C1-C6 alkoksikarbonil, (35) karbamoil C1-C6 alkil koji proizvoljno ima jedan ili dva supstituenta koji se biraju od C1-C6 alkila; morfolinil C1-C6 alkila; piperidila koji proizvoljno ima jedan supstituent koji se bira iz skupine koju čine C1-C6 alkil i C1-C6 alkoksikarbonil; i piperazinil C1-C6 alkil koji proizvoljno ima jednu C1-C6 alkil skupinu, (36) fosfonooksi C1-C6 alkil koji proizvoljno ima jednu ili dvije C1-C6 alkil skupine na fosfono skupini, (37) fosfonooksi C1-C6 alkanoiloksi C1-C6 alkil koji proizvoljno ima jednu ili dvije C1-C6 alkil skupine na fosfono skupini, (38) benzoiloksi C1-C6 alkil koji proizvoljno ima, na benzenskom prstenu, jedan supstituent odabran iz skupine koju čine hidroksi, benziloksi, i fosfonooksi koji proizvoljno ima jednu ili dvije C1-C6 alkil skupine, (39) tetrahidropiranil koji proizvoljno ima jedan do četiri supstituenata koji su odabrani iz skupine koju čine hidroksi, hidroksi C1-C6 alkil i karboksil, ili (40) C1-C6 alkanoilamino C1-C6 alkil koji proizvoljno ima, na C1-C6 alkanoil skupini, jedan ili dva supstituenta odabrana iz skupine koju čine halogen; hidroksi; amino; C1-C6 alkoksikarbonilamino; piperazinil koji proizvoljno ima jednu C1-C6 alkoksi C1-C6 alkil skupinu; imidazolil; i morfolinilpiperidil; R2 predstavlja: (1) vodik, (2) C1-C6 alkil, (3) C1-C6 alkanoil, (4) hidroksi C1-C6 alkil, (5) karboksi, (6) C1-C6 alkoksikarbonil, (7) karbamoil koji proizvoljno ima jedan ili dva supstituenta koji se biraju iz skupine koju čine C1-C6 alkil; halogen-supstituiran C1-C6 alkil; hidroksi C1-C6 alkil; piperazinil C1-C6 alkil koji proizvoljno ima jednu C1-C6 alkil skupinu na piperazinskom prstenu; i morfolinil C1-C6 alkil, (8) karbamoil C1-C6 alkil koji proizvoljno ima jednu C1-C6 alkil skupinu na karbamoil skupini, (9) morfolinil C1-C6 alkil, (10) piperazinil C1-C6 alkil koji proizvoljno ima, na piperazinskom prstenu, jedan supstituent odabran iz skupine koju čine C1-C6 alkil i piridil koji proizvoljno ima jednu C1-C6 alkil skupinu, (11) diazepanil C1-C6 alkil, ili (12) amino C1-C6 alkil koji proizvoljno ima, na amino skupini, jedan ili dva supstituenta odabrana iz skupine koju čine C1-C6 alkil, halogen-supstituiran C1-C6 alkil, hidroksi C1-C6 alkil, i morfolinil C1-C6 alkil; R3 predstavlja fenil, tienil, furil, pirazolil, ili pirimidinil, pri čemu: aromatski ili heterociklički prsten prikazan s R3 može biti supstituiran s jednim ili dva supstituenta odabrana iz skupine koja se sastoji od slijedećih supstituenata (1) do (14) : (1) C1-C6 alkil, (2) C1-C6 alkoksi, (3) C1-C6 alkanoil, (4) halogen, (5) hidroksi, (6) hidroksi C1-C6 alkil, (7) hidroksi C1-C6 alkoksi, (8) tetrahidropiraniloksi C1-C6 alkoksi, (9) karboksi C1-C6 alkoksi, (10) C1-C6 alkoksikarbonil C1-C6 alkoksi, (11) pirolidinilkarbonil, (12) karbamoil C1-C6 alkoksi koji proizvoljno ima jednu ili dvije C1-C6 alkil skupine, (13) karbamoil koji proizvoljno ima jednu morfolinil C1-C6 alkil skupinu, te (14) morfolinilpiperidilkarbonil; R4 predstavlja halogen R5 predstavlja vodik ili halogen; R6 predstavlja vodik ili C1-C6 alkoksi; i R7 predstavlja bilo koju od slijedećih skupina (2) do (11) : (2) C1-C6 alkoksi, (3) hidroksi C1-C6 alkoksi, (4) benziloksi C1-C6 alkoksi, (5) C1-C6 alkoksi C1-C6 alkoksi, (6) karbamoil C1-C6 alkoksi koji proizvoljno ima jedan supstituent koji se bira iz skupine koju čine C1-C6 alkil i morfolinil C1-C6 alkil, (7) amino koji proizvoljno ima jedan ili dva supstituenta koji se biraju iz skupine koju čine C1-C6 alkil i ciklo C3-C8 alkil, (8) ciklo C3-C8 alkiloksi, (9) karboksi C1-C6 alkoksi, (10) C1-C6 alkoksikarbonil C1-C6 alkoksi, i (11) pirolidinil.
2. Spoj kinolona s općom formulom (1) ili njegova sol prema zahtjevu 1, naznačen time da R1 predstavlja: (3) halogen-supstituiran C1-C6 alkil, (4) C2-C6 alkenil, (5) C1-C6 alkanoil, (6) halogen-supstituiran C1-C6 alkanoil, (8) benziloksi C1-C6 alkil, (10) benziloksi C1-C6 alkanoil, (11) C1-C6 alkiltio C1-C6 alkil, (12) amino C1-C6 alkiltio C1-C6 alkil koji proizvoljno ima jednu ili dvije C1-C6 alkil skupine, (13) hidroksi C1-C6 alkiltio C1-C6 alkil, (14) karboksi C1-C6 alkiltio C1-C6 alkil, (15) C1-C6 alkoksikarbonil C1-C6 alkiltio C1-C6 alkil, (16) amino C1-C6 alkiltiokarbonil C1-C6 alkil koji proizvoljno ima jednu ili dvije C1-C6 alkil skupine, (17) hidroksi C1-C6 alkilsulfonil C1-C6 alkil, (18) karboksi C1-C6 alkilsulfonil C1-C6 alkil, (19) C1-C6 alkoksikarbonil C1-C6 alkilsulfonil C1-C6 alkil, (20) C1-C6 alkanoil C1-C6 alkilsulfonil C1-C6 alkil, (21) piperazinil C1-C6 alkilsulfonil C1-C6 alkil koji proizvoljno ima jednu C1-C6 alkil skupinu na piperazinskom prstenu, (22) piperazinilkarbonil C1-C6 alkilsulfonil C1-C6 alkil koji proizvoljno ima jednu C1-C6 alkil skupinu na piperazinskom prstenu, (24) karboksi C1-C6 alkil, (25) C1-C6 alkoksikarbonil C1-C6 alkil, (26) piperazinil C1-C6 alkoksikarbonil C1-C6 alkil koji proizvoljno ima jednu C1-C6 alkil skupinu na piperazinskom prstenu, (27) morfolinil C1-C6 alkil, (29) amino C1-C6 alkil koji proizvoljno ima jednu ili dvije C1-C6 alkil skupine, (30) piperazil C1-C6 alkil koji proizvoljno ima, na piperazinskom prstenu, jedan supstituent odabran iz skupine koju čine C1-C6 alkil, C1-C6 alkoksi C1-C6 alkil, i piridil, (31) piperidil C1-C6 alkil koji proizvoljno ima jednu morfolinil skupinu, (32) azetidil C1-C6 alkil koji proizvoljno ima jednu hidroksi skupinu na azetidinskom prstenu, (33) izoindolinil C1-C6 alkil koji proizvoljno ima jednu ili dvije okso skupine, (34) amino C1-C6 alkanoiloksi C1-C6 alkil koji proizvoljno ima jedan ili dva supstituenta koji se biraju iz skupine koju čine C1-C6 alkil i C1-C6 alkoksikarbonil, (35) karbamoil C1-C6 alkil koji proizvoljno ima jedan ili dva supstituenta koji se biraju od C1-C6 alkil; morfolinil C1-C6 alkil; piperidil koji proizvoljno ima jedan supstituent koji se bira iz skupine koju čine C1-C6 alkil i C1-C6 alkoksikarbonil; i piperazinil C1-C6 alkil koji proizvoljno ima jednu C1-C6 alkil skupinu, (36) fosfonooksi C1-C6 alkil koji proizvoljno ima jednu ili dvije C1-C6 alkil skupine na fosfono skupini, (37) fosfonooksi C1-C6 alkanoiloksi C1-C6 alkil koji proizvoljno ima jednu ili dvije C1-C6 alkil skupine na fosfono skupini, (38) benzoiloksi C1-C6 alkil koji proizvoljno ima, na benzenskom prstenu, jedan supstituent odabran iz skupine koju čine hidroksi, benziloksi, i fosfonooksi koji proizvoljno ima jednu ili dvije C1-C6 alkil skupine, (39) tetrahidropiranil koji proizvoljno ima jedan ili četiri supstituenata odabrana iz skupine koju čine hidroksi, hidroksi C1-C6 alkil i karboksil, ili (40) C1-C6 alkanoilamino C1-C6 alkil koji proizvoljno ima, na C1-C6 alkanoil skupini, jedan ili dva supstituenta odabrana iz skupine koju čine halogen; hidroksi; amino; C1-C6 alkoksikarbonilamino; piperazinil koji proizvoljno ima jednu C1-C6 alkoksi C1-C6 alkil skupinu; imidazolil; i morfolinilpiperidil; R2 predstavlja vodik; R3 predstavlja fenil, pirazolil, ili pirimidinil, pri čemu: aromatski ili heterociklički prsten prikazan s R3 može biti supstituiran s jednim ili dva supstituenta odabrana iz skupine koja se sastoji od slijedećih supstituenata (1), (2), (4), (5), (7), (8), (10), (11), i (12): (1) C1-C6 alkil, (2) C1-C6 alkoksi, (4) halogen, (5) hidroksi, (7) hidroksi C1-C6 alkoksi, (8) tetrahidropiraniloksi C1-C6 alkoksi, (10) C1-C6 alkoksikarbonil C1-C6 alkoksi, (11) pirolidinilkarbonil, i (12) karbamoil C1-C6 alkoksi; R4 predstavlja halogen; R5 predstavlja vodik ili halogen; R6 predstavlja vodik; i R7 predstavlja bilo koju od slijedećih skupina (2), (7), (8) i (11): (2) C1-C6 alkoksi, (7) amino koji proizvoljno ima jedan ili dva supstituenta koji se biraju iz skupine koju čine C1-C6 alkil i ciklo C3-C8 alkil, (8) ciklo C3-C8 alkiloksi, i (11) pirolidinil.
3. Spoj kinolona prema zahtjevu 1, naznačen time da sadrži Primjer 188 [image] Primjer 189 [image] Primjer 190 [image] Primjer 191 [image] Primjer 192 [image] Primjer 193 [image] Primjer 194 [image] Primjer 195 [image] Primjer 196 [image] Primjer 197 [image] Primjer 198 [image] Primjer 199 [image] Primjer 200 [image] Primjer 201 [image] Primjer 202 [image] Primjer 203 [image] Primjer 204 [image] Primjer 205 [image] Primjer 206 [image] Primjer 207 [image] Primjer 208 [image] Primjer 209 [image] Primjer 210 [image] Primjer 211 [image] Primjer 212 [image] Primjer 213 [image] Primjer 214 [image] Primjer 215 [image] Primjer 216 [image] Primjer 217 [image] Primjer 218 [image] Primjer 219 [image] Primjer 220 [image] Primjer 221 [image] Primjer 222 [image] Primjer 223 [image] Primjer 252 [image] Primjer 253 [image] ili Primjer 254 [image]
4. Farmaceutski pripravak naznačen time da sadrži spoj kinolona s općom formulom (1) prema bilo kojem od zahtjeva 1 do 3 ili njegovu sol kao aktivni sastojak; i farmaceutski prihvatljiv nosač.
5. Sredstvo za primjenu za profilaktičko i/ili terapeutsko liječenje neurodegenerativnih bolesti potaknutih s neurološkom disfunkcijom bolesti ili bolesti potaknutih slabljenjem funkcije mitohondrija, naznačeno time da sredstvo kao aktivni sastojak sadrži spoj kinolona s općom formulom (1) prema bilo kojem od zahtjeva 1 do 3 ili njegovu sol.
6. Sredstvo za primjenu za profilaktičko i/ili terapeutsko liječenje prema zahtjevu 5, naznačeno time da se neurodegenerativna bolest bira iz skupine koju čine Parkinsonova bolest, Parkinsonov sindrom, juvenilni parkinsonizam, striatonigralna degeneracija, progresivna supranuklearna paraliza, akinezija, Alzheimerova bolest, Pickova bolest, prionska bolest, kortikobazalna degeneracija, difuzna bolest Lewyevih tjelešaca, Huntingtonova bolest, koreja-akantocitoza, benigna nasljedna koreja, paroksizmalna koreoatetoza, esencijalni tremor, esencijalni mioklonus, Gilles de la Touretteov sindrom, Rettov sindrom, degenerativni balizam, dystonia musculorum deformans, atetoza, spazmodički tortikolis, Meigeov sindrom, cerebralna paraliza, Wilsonova bolest, Segawaina bolest, Hallervorden-Spatzov sindrom, neuroaksonalna distrofija, palidalna atrofija, spinocerebelarna degeneracija, cerebralna kortikalna atrofija, cerebelarna atrofija Holmesovog tipa, olivopontocerebelarna atrofija, nasljedna olivopontocerebelarna atrofija, Josephova bolest, dentato-rubro-palido-luisna atrofija, Gerstmann-Straussler-Scheinkerova bolest, Friedreichova ataksija, Roussy-Levyjev sindrom, May-Whiteov sindrom, kongenitalna cerebelarna ataksija, nasljedna epizodična ataksija, ataksija teleangiektazija, amiotrofična lateralna skleroza, progresivna bulbarna paraliza, progresivna spinalna mišićna atrofija, spinobulbarna mišićna atrofija, Werdnig-Hoffmannova bolest, Kugelberg-Welanderova bolest, nasljedna spastička parapareza, siringomijelija, siringobulbija, Arnold-Chiarijeva malformacija, Stiffmanov sindrom, Klippel-Feilov sindrom, Fazio-Londeov sindrom, mijelopatija donjeg dijela, Dandy-Walkerov sindrom, spina bifida, Sjogren-Larssonov sindrom, radijacijska mijelopatija, makularna degeneracija povezana s dobi i cerebralna apopleksija, odabrana iz skupine koju čine cerebralni infarkt i cerebralno krvarenje i/ili povezane disfunkcije ili neurološki deficiti.
7. Sredstvo za primjenu za profilaktičko i/ili terapeutsko liječenje prema zahtjevu 5, naznačeno time da je bolest potaknuta neurološkom disfunkcijom odabrana iz skupine koju čine: oštećenje kičmene moždine, neuropatija potaknuta kemoterapijom, dijabetička neuropatija, oštećenje uslijed radijacije i demijelinizacijske bolesti odabrane iz skupine koju čine multipla skleroza, akutni diseminirani encefalomijelitis, transverzni mijelitis, progresivna multifokalna leukoencefalopatija, subakutni sklerozni panencefalitis, kronična inflamatorna demijelinizacijska polineuropatija i Guillain-Barreov sindrom.
8. Sredstvo za primjenu za profilaktičko i/ili terapeutsko liječenje prema zahtjevu 5, naznačeno time da je bolest potaknuta slabljenjem funkcije mitohondrija odabrana iz skupine koju čine: Pearsonov sindrom, dijabetes, gluhoća, maligna migrena, Leberova bolest, MELAS, MERRF, sindrom preklapanja MERRF/MELAS, NARP, čista miopatija, mitohondrijalna kardiomiopatija, miopatija, demencija, gastrointestinalna ataksija, stečena sideroblastična anemija, gubitak sluha potaknut aminoglikozidima, deficijencija kompleksa III zbog naslijeđenih varijanti citokroma b, multipla simetrična lipomatoza, ataksija, mioklonus, retinopatija, MNGIE, bolest ANT1, Twinkleova bolest, bolest POLG, rekurentna mioglobinurija, SANDO, ARCO, deficijencija kompleksa I, deficijencija kompleksa II, atrofija očnog živca, fatalna dječja deficijencija kompleksa IV, deficijencija mitohondrijske DNA, sindrom deficijencije mitohondrijske DNA, Leighova encefalomijelopatija, sindrom kronične progresivne vanjske oftalmoplegije (CPEO), Kearns-Sayreov sindrom, encefalopatija, laktacidemija, mioglobinurija, mitohondrijske bolesti potaknute lijekovima, shizofrenija, poremećaj teške depresije, bipolarni poremećaj tip I, bipolarni poremećaj tip II, distimični poremećaji s pomiješanim epizodama, atipična depresija, sezonski afektivni poremećaji, postporođajna depresija, lakša depresija, rekurentni kratki depresivni poremećaj, intraktabilna depresija/kronična depresija, dvostruka depresija i akutno zatajenje bubrega.
9. Sredstvo za primjenu za profilaktičko i/ili terapeutsko liječenje naznačeno time da kao aktivni sastojak sadrži spoj prema bilo kojem od zahtjeva 1 do 3 ili njegovu sol, te se profilaktičko i/ili terapeutsko sredstvo koristi za liječenje ili prevenciju ishemijskih bolesti srca i/ili povezane disfunkcije, zatajenja srca, miokarditisa, disekcije aorte, imunodeficijencije, autoimunih bolesti, insuficijencije gušterače, dijabetesa, ateroembolijske bolesti bubrega, policistične bolesti bubrega, medularne cistične bolesti, bubrežne kortikalne nekroze, maligne nefroskleroze, zatajenja bubrega, jetrene encefalopatije, zatajenja jetre, kronične opstruktivne plućne bolesti, plućne embolije, bronhiektazije, silikoze, bolesti crnih pluća, idiopatske plućne fibroze, Stevens-Johnsonovog sindroma, toksične epidermalne nekrolize, mišićne distrofije, bakterijskih mišićne nekroze, te femoralne kondilne nekroze.
10. Postupak za proizvodnju spoja kinolona prikazanog s Formula (1b): [image] pri čemu R2, R3, R4, R5, R6, i R7 su kako je definirano u zahtjevu 1, i R1' je skupina prikazana s R1 kako je definirano u zahtjevu 1, ili njegova sol; te postupak sadrži reakciju spoja prikazanog s formulom: R1' -X2 pri čemu X2 predstavlja skupinu koja prolazi kroz istu supstitucijsku reakciju kao i halogen ili halogeni atom, sa spojem prikazanim s formulom: [image] pri čemu R2, R3, R4, R5, R6 i R7 su kako je definirano u zahtjevu 1.
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