ME01422B - Derivati benzola supstituisani glukopiranozilom, ljekovi koji sadrže navedena jedinjenja, njihova primjena i njihov postupak proizvodnje - Google Patents

Derivati benzola supstituisani glukopiranozilom, ljekovi koji sadrže navedena jedinjenja, njihova primjena i njihov postupak proizvodnje

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Publication number
ME01422B
ME01422B MEP-2012-72A MEP7212A ME01422B ME 01422 B ME01422 B ME 01422B ME P7212 A MEP7212 A ME P7212A ME 01422 B ME01422 B ME 01422B
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Montenegro
Prior art keywords
alkyl
substituted
groups
group
aryl
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MEP-2012-72A
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German (de)
English (en)
French (fr)
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Frank Himmelsbach
Matthias Eckhardt
Leo Thomas
Peter Eickelmann
Edward Leon Barsoumian
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Boehringer Ingelheim Int
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=34962236&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=ME01422(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority claimed from DE102004012676A external-priority patent/DE102004012676A1/de
Priority claimed from DE102004040168A external-priority patent/DE102004040168A1/de
Priority claimed from DE102004061145A external-priority patent/DE102004061145A1/de
Application filed by Boehringer Ingelheim Int filed Critical Boehringer Ingelheim Int
Publication of ME01422B publication Critical patent/ME01422B/me

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Claims (47)

1. Derivati benzola supstituisani glukopiranozilom opšte formule I u kojoj R1 je izabrano između sledećih značenja: vodonik, fluor, hlor, brom, jod, C1-4-alkil, C2-6-alkinil, C1-4-alkoksi, C2-4-alkenil-C1-4-alkoksi, C2-4-alkinil-C1-4-alkoksi, metil grupa supstituisana sa 1 do 3 atoma fluora, etil grupa supstituisana sa 1 do 5 atoma fluora, metoksi grupa supstituisana sa 1 do 3 atoma fluora, etoksi grupa supstituisana sa 1 do 5 atoma fluora, C1-4-alkil grupa supstituisana sa hidroksi- ili C1-3-alkoksi grupom, C2-4-alkoksi grupa supstituisana sa hidroksi- ili C1-3-alkoksi grupom, C2-4-alkenil, C3-6-cikloalkil, C3-6-cikloalkil-C1-3-alkil, C3-7- cikloalkoksi, C3-7-cikloalkil-C1-3-alkoksi, C5-7-cikloalkeniloksi, hidroksi, amino, nitro ili cijano, pri čemu u C5-6-cikloalkil grupama metilen grupa može biti zamenjena sa O, R2 označava vodonik, fluor, hlor, brom, hidroksi, C1-4-alkil, C1-4-alkoksi, cijano ili nitro, pri čemu alkil- ili alkoksi grupa može biti jednostruko ili višestruko supstituisana sa fluorom, i R3 je izabrano između sledećih značenja: tri-(C1-4-alkil)silil-C1-6-alkil, C1-4- alkin-1 -il, C1-4-alken-1-il, amino, C1-3-alkilamino, di-(C1-3-alkil)amino, pirolidin-1-il, pirolidin-2-on-1 -ii, piperidin-1-il, piperidin-2-on-1-il, morfolin- 4-il, morfolin-3-on-4-il, piperazin-1 -il, 4-(C1-3-alkil)piperazin-1-il, nitro, C3- 7-cikloalkiloksi, C5-7-cikloalkeniloksi, C5-7-cikloalkilsulfanil, C5-7- cikloalkilsulfinil, C5-7-cikloalkilsulfonil, C5-7-cikloalkenilsulfanil, C5-7- cikloalkenilsulfinil, C5-7-cikloalkenilsulfonil, pri čemu napred navedene alkinil i alkenil grupe mogu biti jednostruko ili dvostruko supstituisane sa fluorom ili hlorom, a prvenstveno sa fluorom, i pri čemu napred navedene alkinil i alkenil grupe mogu biti jednostruko ili dvostruko supstituisane sa istim ili različitim radikalima L1, pri čemu napred navedeni cikloalkil i cikloalkenil prstenovi nezavisno jedan od drugog mogu biti jednostruko ili dvostruko supstituisani sa fluorom i C1-3-alkilom, i pri čemu u napred navedenim cikloalkil i cikloalkenil prstenovima jedna ili dve metilen grupe nezavisno jedna od druge mogu biti zamenjene sa O, S, CO, SO, SO2 ili NRN, a prvenstveno sa O, CO, S, S02 ili NRN, te najpoželjnije sa O ili CO, R4, R5 nezavisno jedna od drugog označavaju vodonik, fluor, hlor, brom, jod, cijano, nitro, C1-3-alkil, C1-3-alkoksi, metil ili metoksi koji su supstituisani sa 1 do 3 atoma fluora, Rn označava H, C1-4-alkil, C1-4-alkilkarbonil ili C1-4-alkilsulfonil, L1 su nezavisno jedan od drugog izabrani iz grupe koja se sastoji od sledećih: hidroksi-, cijano-, nitro-, C3-7-cikloalkil, aril-, heteroaril-, C1-4- alkilkarbonil-, arilkarbonil-, heteroarilkarbonil-, aminokarbonil-, C1-4- alkilaminokarbonil-, di-(C1-3-alkil) aminokarbonil-, pirolidin-1 -ilkarbonil-, piperidin-1-ilkarbonil-, morfolin-4-ilkarbonil, arilaminokarbonil-, heteroarilamino-karbonil-, C1-4-alkoksikarbonil-, aril-C1-3-alkoksikarbonil-, heteroaril-C1-3-alkoksikarbonil-, C1-4-alkiloksi-, ariloksi-, heteroariloksi-, C1-4-alkilsulfanil-, arilsulfanil-, heteroarilsulfanil-, C1-4-alkilsulfinil-, arilsulfinil-, heteroarilsulfinil-, C1-4- alkilsulfonil-, arilsulfonil- i heteroarilsulfonil-; i L2 su nezavisno jedan od drugog izabrani iz grupe koja se sastoji od sledećih: fluor, hlor, brom, jod, C1-3-alkil, difluormetil, trifluormetil, C1-3- alkoksi, difluormetoksi, trifluormetoksi i cijano; i R6 označava vodonik, (C1-6-alkil)oksikarbonil ili C1-6-alkilkarbonil, R7a, R7b, R7c označavaju vodonik, pri čemu se pod aril grupama pomenutim u definiciji gore navedenih radikala podrazumevaju fenil ili naftil grupe, koje nezavisno jedna od druge mogu biti jednostruko ili dvostruko supstituisane sa istim ili različitim radikalima L2; i pod heteroaril grupama pomenutim u definiciji gore navedenih radikala se podrazumevaju pirolil, furanil, tienil, piridil, indolil, benzofuranil, benzotiofenil, hinolinil, izohinolinil ili tetrazolil grupa, ili se podrazumeva pirolil, furanil, tienil ili piridil grupa, u kojoj su jedna ili dve metin grupe zamenjene sa atomom azota, ili se podrazumeva indolil, benzofuranil, benzotiofenil, hinolinil ili izohinolinil grupa, u kojoj su jedna do tri metin grupe zamenjene sa atomom azota, pri čemu napred navedene heteroaril grupe nezavisno jedna od druge mogu biti jednostruko ili dvostruko supstituisane sa istim ili različitim radikalima L2; pri čemu, ukoliko nije drugačije navedeno, gore navedene alkil grupe mogu biti linearne ili razgranate, njihovi tautomeri, njihovi stereoizomeri, njihove smeše i njihove soli.
2.Derivati benzola supstituisani glukopiranozilom opšte formule 1.2 u kojoj su radikali R1 do R1 i R7a, R7b i R7C definisani isto kao u zahtevu 1.
3.Derivati benzola supstituisani glikopiranozilom opšte formule 1.2c u kojoj su radikali R1 do R6 i R7a, R7b i R7C definisani isto kao u zahtevu 1.
4.Derivati benzola supstituisani glukopiranozilom prema jednom ili više zahteva 1 do 3, naznačeni time, što je grupa R1 izabrana između sledećih značenja: vodonik, fluor, hlor, brom, cijano, metil, etil, izopropil, difluormetil, trifluormetil, etinil, prop-1-in-1-il, but-1-in-1-il, hidroksi, metoksi, etoksi, difluormetoksi, ciklopropiloksi, ciklobutiloksi, ciklopentiloksi, cikloheksiloksi.
5.Derivati benzola supstituisani glukopiranozilom prema zahtevu 1, 2 ili 3, naznačeni time, što je grupa R1 izabrana između sledećih značenja: metil i hlor.
6. Derivati benzola supstituisani glukopiranozilom prema jednom ili više zahteva 1 do 5, naznačeni time, što je grupa R3 izabrana između sledećih značenja: tri- (C1-4-alkiljsilil-C1-6-alkil, C2-6-alkin-1-il, C2-6-alken-1-il, C3-7-cikloalkoksi, C5-7- cikloalkeniloksi, C3-7-cikloalkilsulfanil, C5-7-cikloalkenilsulfanil, pri čemu napred navedene alkinil i alkenil grupe mogu biti jednostruko ili višestruko supstituisane sa fluorom ili jednostruko sa hlorom ili sa radikalom L1, i pri čemu u cikloalkil i cikloalkenil grupama jedna ili dve metilen grupe mogu biti zamenjene nezavisno jedna od druge sa O, CO, S, SO2 ili NRN, a naročito sa O ili CO, i L1 i Rn su definisani isto kao u zahtevu 1.
7.Derivati benzola supstituisani glukopiranozilom prema jednom ili više zahteva 1 do 5, naznačeni time, što je grupa R3 izabrana između sledećih značenja: trimetilsililetil, etinil, 1-propin-1-il, 1-butin-1-il, terc.-butiletinil, 2-hidroksiprop-2- iletinil, 2-metoksiprop-2-iletinil, 3-hidroksi-1-propin-1-il, 3-metoksi-1-propin-1-il, etenil, 1-propenil, 1-butenil, terc.-butiletenil, ciklopropiloksi, ciklobutiloksi, ciklopentiloksi, cikloheksiloksi, tetrahidrofuraniloksi, tetrahidrotiofeniloksi, 1,1- dioksotetrahidro-tiofeniloksi, tetrahidropiraniloksi, tetrahidrotiopiraniloksi, 1,1- dioksotetrahidrotiopiraniloksi, tetrahidrofuranoniloksi, piperidiniloksi, piperidinoniloksi, pirolidin-3-iloksi, pirolidinon-3-iloksi, tetrahidrofuranil-sulfanil, ciklopropilsulfanil, ciklobutilsufanil, ciklopentilsulfanil i cikloheksilsulfanil, pri čemu -NH grupa u piperidinil, piperidinonil, pirolidinil ili pirolidinonil prstenu može biti supstituisana sa C1-3-alkilom ili acetilom.
8.Derivati benzola supstituisani glukopiranozilom prema jednom ili više zahteva 1 do 5, naznačeni time, što je grupa R3 izabrana između sledećih značenja: trimetilsililetil, etinil, 2-hidroksiprop-2-iletinil, 2-metoksiprop-2-iletinil, 3-hidroksi- 1 -propin-1-il, 3-metoksi-1-propin-1-il, ciklopropiloksi, ciklobutiloksi, ciklopentiloksi, cikloheksiloksi, tetrahidrofuran-3-iloksi, tetrahidropiran-4-iloksi, piperidin-4-iloksi, N-metilpiperidin-4-iloksi i N-acetilpiperidin-4-iloksi.
9.Derivati benzola supstituisani glukopiranozilom prema jednom ili više zahteva 1 do 5, naznačeni time, što je grupa R3 izabrana između sledećih značenja: etinil, trimetilsililetil, ciklobutiloksi, ciklopentiloksi, cikloheksiloksi, tetrahidrofuran-3-iloksi i tetrahidropiran-4-iloksi.
10.Derivati benzola supstituisani glukopiranozilom prema jednom ili više zahteva 1 do 9, naznačeni time, što radikal R2 označava vodonik, fluor, hlor, brom, metil, hidroksi, metoksi, etoksi, trifluormetoksi, cijano, nitro ili metil koji je supstituisan sa 1 do 3 atoma fluora.
11.Derivati benzola supstituisani glukopiranozilom prema zahtevu 10, naznačeni time, što radikal R2 označava vodonik ili metil.
12.Derivati benzola supstituisani glukopiranozilom prema jednom od zahteva 1 do 11, naznačeni time, što radikali R4 i/ili R5 nezavisno jedan od drugog označavaju vodonik ili fluor.
13.Derivati benzola supstituisani glukopiranozilom prema zahtevu 12, naznačeni time, što radikal R4 označava vodonik.
14.Derivati benzola supstituisani glukopiranozilom prema zahtevu 12, naznačeni time, što radikal R5 označava vodonik.
15.Derivati benzola supstituisani glukopiranozilom prema jednom od zahteva 1 do 13, naznačeni time, što radikal R6 označava vodonik.
16.Derivati benzola supstituisani glukopiranozilom prema jednom od zahteva 1, 2, 3, 4 ili 10, naznačeni time, što radikal RN označava H, metil, etil ili acetil.
17.Derivati benzola supstituisani glukopiranozilom prema jednom ili više zahteva 1 do 16, naznačeni time, što je radikal L1 izabran iz grupe koja se sastoji od sledećih: hidroksi-, cijano-, C3-6-cikloalkil, C1-4-alkilkarbonil-, aminokarbonil-, C1-4-alkilaminokarbonil-, di-(C1-3-alkil)aminokarbonil-, pirolidin-1-ilkarbonil-, piperidin-1 -ilkarbonil-, morfolin-4-ilkarbonil, C1-4-alkoksikarbonil-, C1-4-alkiloksi-, C1-4-alkilsulfanil-, C1-4-alkilsulfinil- i C1-4-alkilsulfonil-.
18.Derivati benzola supstituisani glukopiranozilom prema jednom ili više zahteva 1 do 16, naznačeni time, što je radikal L1 izabran iz grupe koja se sastoji od sledećih: hidroksi, C1-4-alkiloksi- i C1-4-alkilsulfanil-.
19.Derivati benzola supstituisani glukopiranozilom prema jednom ili više zahteva 1 do 18, koji su izabrani iz grupe jedinjenja (1) do (8), (10) do (15) i (17): (1)1-hlor-2-(4-ciklopentiloksibenzil)-4-(p-D-glukopiranoz-1-il)-benzol (2)1-hlor-4-(p-D-glukopiranoz-1-il)-2-[4-((R)-tetrahidrofuran-3-iloksi)-benzil]- benzol (3)1-hlor-4-(P-D-glukopiranoz-1-il)-2-[4-((S)-tetrahidrofuran-3-iloksi)-benzil]- benzol (4)1-hlor-4-(P-D-glukopiranoz-1-il)-2-[4-(tetrahidrofuran-2-on-3-iloksi)- benzil]- benzol (5)1-hlor-4-(P-D-glukopiranoz-1-il)-2-(4-ciklobutiloksi-benzil)-benzc (6)1 -hlor-4-(P-D-glukopiranoz-1 -il)-2-(4-cikloheksiloksi-benzil)-benzol (7)1-hlor-4-(P-D-glukopiranoz-1-il)-2-[4-(tetrahidropiran-4-iloksi)-benzil]- benzol (8)1-hlor-4-(P-D-glukopiranoz-1-il)-2-[4-(1-acetil-piperidin-4-iloksi)-benzil]- benzol (10)1- (P-D-glukopiranoz-1-il)-4-metil-3-[4- (tetrahidrofuran-3-iloksi)-benzilj- benzol (11)1- (P-D-glukopiranoz-1-il)-4-metil-3-[4-(2-trimetilsilil-etil)-benzil]-benzol (12)1-hlor-4-(P-D-glukopiranoz-1-il)-2-(4-etinil-benzil)-benzol (13)1 -hlor-4-(P-D-glukopiranoz-1 -il)-2-[4-(piperdin-4-iloksi)-benzil]-benzol (14)1 -fluor-4-(P-D-glukopiranoz-1 -il)-2-(4-etinil-benzil)-benzol (15)1- (P-D-glukopiranoz-1-il)-3-(4-etinil-benzil)-benzol (17) 1-metoksi-4-(P-D-glukopiranoz-1-il)-2-(4-etinil-benzil)-benzol
20.Derivati benzola supstituisani glukopiranozilom prema zahtevu 19, naznačeni time što je derivat benzola supstituisan glukopiranozilom jedinjenje (2): (2) 1-hlor-4-(P-D-glukopiranoz-1-il)-2-[4-((R)-tetrahidrofuran-3-iloksi)-benzil]- benzol.
21.Derivati benzola supstituisani glukopiranozilom prema zahtevu 19, naznačeni time što je derivat benzola supstituisan glukopiranozilom jedinjenje (3): (3)1 -hlor-4-(P-D-glukopiranoz-1 -il)-2-[4-((S)-tetrahidrofuran-3-iloksi)-benzilj- benzol.
22.Fiziološki prihvatljive soli jedinjenja prema najmanje jednom od zahteva 1 do 21 sa neorganskim ili organskim kiselinama.
23.Lek koji sadrži jedinjenje prema najmanje jednom od zahteva 1 do 21 ili fiziološki prihvatljivu so prema zahtevu 22, eventualno sa jednim ili više inertnih nosača i/ili razređivača.
24.Primena najmanje jednog jedinjenja prema najmanje jednom od zahteva 1 do 21 ili fiziološki prihvatljive soli prema zahtevu 22 za dobijanje leka koji je podesan za tečenje ili prevenciju metaboličkih poremećaja koji su izabrani između sledećih: dijabetes melitus tip 1 i tip 2, dijabetesne komplikacije, metabolička acidoza ili ketoza, reaktivna hipoglikemija, hiperinsulinemija, metabolički poremećaj glukoze, rezistencija na insulin, metabolički sindrom, dislipidemije različitog porekla, ateroskleroza i srodne bolesti, gojaznost, visoki krvni pritisak, hronična srčana insuficijencija, edemi i hiperurikemija.
25.Primena prema zahtevu 24, naznačena time što je metabolički poremećaj izabran između dijabetes melitusa tip 1 i tip 2 i dijabetesnih komplikacija.
26.Primena najmanje jednog jedinjenja prema najmanje jednom od zahteva 1 do 21 ili fiziološki prihvatljive soli prema zahtevu 22 za dobijanje leka za inhibiciju kotransportera glukoze zavisnog od natrijuma SGLT2.
27.Primena najmanje jednog jedinjenja prema najmanje jednom od zahteva 1 do 21 ili fiziološki prihvatljive soli prema zahtevu 22 za dobijanje leka za prevenciju degeneracije pankreasnih beta ćelija i/ili za poboljšanje i/ili povraćaj funkcionalnosti pankreasnih beta ćelija.
28.Primena najmanje jednog jedinjenja prema najmanje jednom od zahteva 1 do 21 ili fiziološki prihvatljive soli prema zahtevu 22 za dobijanje diuretika i/ili antihipertenziva.
29. Postupak za dobijanje jedinjenja opšte formule I prema zahtevima 1 do 21, naznačen time što jedinjenje opšte formule II u kojoj R' označava H, C1-4-alkil, (C1-18-alkil)karbonil, (C1-18-alkil)- oksikarbonil, arilkarbonil ili aril-(C1-3-alkil)-karbonil, pri čemu alkil ili aril grupe mogu biti jednostruko ili višestruko supstituisane sa halogenom; R8a R8b R8c R8d su nezavisno jedan od drugog izabrani iz grupe sledećih: vodonik, (C1-18-alkil)karbonil, (C1-18-alkil)oksikarbonil, arilkarbonil i aril-(C1-3-alkil)-karbonil, ili označavaju benzil grupu ili RaRbRcSi grupu ili ketal ili acetal grupu, pri čemu dva susedna radikala R8a, R8b, R8c, R8d mogu uvek obrazovati cikličnu ketal- ili acetal- grupu ili 1,2-di(C1-3-alkoksi)-1,2-di(C1-3-alkil)-etilenski most, pri čemu gore navedeni etilenski most obrazuje zajedno sa dva atoma kiseonika i dva pripadajuća atoma ugljenika piranoznog prstena supstituisani dioksanski prsten, i pri čemu alkil, aril i/ili benzil grupe mogu biti jednostruko ili višestruko supstituisane sa halogenom ili C1-3-alkoksi, a benzil grupe mogu takođe biti supstituisane sa di-(C1-3-alkil)amino grupom; i Ra, Rb, Rc nezavisno jedan od drugog označavaju C1-4-alkil, aril ili aril-C1-4- alkil, pri čemu alkil ili aril grupe mogu biti jednostruko ili višestruko supstituisane sa halogenom; pri čemu se pod aril grupama koje su pomenute u definiciji gore navedenih grupa podrazumevaju fenil ili naftil grupe, a prvenstveno fenil grupe; i R1 do R5 imaju ista značenja koja su data u zahtevima 1 do 21, reaguje sa agensom za redukciju u prisustvu Luisove ili Brenstedove kiseline, pri čemu se zaštitne grupe koje su eventualno prisutne odvajaju istovremeno ili posle toga; ukoliko je potrebno, ovako dobijeno jedinjenje opšte formule I, u kojoj R6 označava atom vodonika, konvertuje se acilovanjem u odgovarajuće acil jedinjenje opšte formule I, i/ili ukoliko je potrebno, zaštitna grupa koja je eventualno upotrebljena u gore opisanim reakcijama se odvaja i/ili ukoliko je potrebno, ovako dobijeno jedinjenje opšte formule I se razdvaja na svoje stereoizomere i/ili ukoliko je potrebno, ovako dobijeno jedinjenje opšte formule I se konvertuje u svoje fiziološki prihvatljive soli.
30.Postupak prema zahtevu 29, naznačen time što se jedinjenje opšte formule II dobija postupkom koji je opisan u zahtevima 31 ili 32.
31.Postupak za dobijanje jedinjenja opšte formule II u kojoj [1] R' označava H, C1-4-alkil, (C1-18-alkil)karbonil, (C1-18- alkil)oksikarbonil, arilkarbonil ili aril-(C1-3-alkil)-karbonil, pri čemu alkil- ili aril- grupe mogu biti jednostruko ili višestruko supstituisane sa halogenom; R8c, R8d su nezavisno jedan od drugog izabrani između sledećih: vodonik, (C1-18-alkil)karbonil, (C1-18-alkil)oksikarbonil, arilkarbonil i aril-(C1-3-alkil)-karbonil, ili označavaju benzil grupu ili RaRbRcSi grupu ili ketal ili acetal grupu, pri čemu dve susedne grupe R8a, R8b, R8c, R8d mogu uvek obrazovati cikličnu ketal- ili acetal- grupu ili 1,2-di(C1-3-alkoksi)-1,2-di(C1-3-alkil)-etilenski most, pri čemu gore navedeni etilenski most obrazuje, zajedno sa dva atoma kiseonika i dva pripadajuća atoma ugljenika piranoznog prstena, supstituisani dioksanski prsten, i pri čemu alkil, aril i/ili benzil grupe mogu biti jednostruko ili višestruko supstituisane sa halogenom ili C1-3-alkoksi i benzil grupe mogu takođe biti supstituisane sa di-(C1-3-alkil)amino grupom; i Ra, Rb, Rc nezavisno jedan od drugog označavaju C1-4-alkil, aril ili aril-C1-3-alkil, pri čemu aril ili alkil grupe mogu biti jednostruko ili višestruko supstituisane sa halogenom; pri čemu se pod aril grupama koje su pomenute u definiciji gore navedenih grupa podrazumevaju fenil ili naftil grupe, a prvenstveno fenil grupe; i R1 do R5 imaju ista značenja koja su data u zahtevima 1 do 21, pri čemu jedno organometalno jedinjenje (V) koje se može dobiti razmenom halogen-metal ili ubacivanjem metala u vezu ugljenik-halogen u halogen-benzil- benzenskom jedinjenju opšte formule IV u kojoj Hal označava Cl, Br i I i R1 do R5 su isti kao što je gore definisano, i eventualno pratećom transmetalacijom, dodaje se glukonolakton opšte formule VI, pri čemu su R8a, R8b, R8c, R8d isti kao što je gore definisano, i onda tako dobijeni adukt reaguje sa vodom ili alkoholom R'-OH, pri čemu R' označava eventualno supstituisani C^-alkil, u prisustvu kiseline i eventualno se proizvod dobijen u reakciji sa vodom, pri čemu R' označava H, u narednoj reakciji sa acilujućim agensom konvertuje u proizvod formule II, u kojoj R' označava (C^a-alkiljkarbonil, (C1-18-alkil)oksikarbonil, arilkarbonil ili aril-(C1-3- alkilj-karbonil, koji može biti supstituisan kao što je specifikovano.
32.Postupak prema zahtevu 31, naznačen time što je organometalno jedinjenje (V) jedinjenje litijuma ili magnezijuma.
33.Postupak za dobijanje jedinjenja opšte formule I prema zahtevima 1 do 21, u kojoj R6 označava vodonik, naznačen time što jedinjenje opšte formule III u kojoj p8a p8b R8c, R8d su nezavisno jedan od drugog izabrani između sledećih: vodonik, (C1-18-alkiljkarbonil, (C1-18-alkil)oksikarbonil, arilkarbonil i aril-(C1-3-alkil)-karbonil, ali najmanje jedan od radikala R8a, R8b, r8c R8d ne označava vodonik, ili označava benzil grupu, dok dve susedne grupe R8a, R8b, R8c, R8d mogu uvek obrazovati cikličnu ketal ili acetal grupu ili 1,2-di(C1-3-alkoksi)-1,2-di(C1-3-alkil)- etilenski most, pri čemu gore navedeni etilenski most obrazuje supstituisani dioksanski prsten zajedno sa dva atoma kiseonika i pridruženim dva atoma ugljenika piranoznog prstena, i pri čemu alkil, ari I i/ili benzil grupe mogu biti jednostruko ili višestruko supstituisane sa halogenom ili C1-3-alkoksi, a benzil grupe mogu biti takođe supstituisane sa di-(C1-3-alkil)amino grupom; i Ra, Rb, Rc nezavisno predstavljaju C1-4-alkil, aril ili aril-C1-4-alkil, pri čemu alkil ili aril grupe mogu biti jednostruko ili višestruko supstituisane sa halogenom; pri čemu se pod aril grupama koje su pomenute u definiciji gore navedenih grupa podrazumevaju fenil ili naftil grupe, a prvenstveno fenil grupe; i R1 do R5 imaju značenja koja su data u zahtevima 1 do 21, se hidrolizuje, i ukoliko je potrebno, ovako dobijeno jedinjenje opšte formule I u kojoj R6 označava atom vodonika, acilovanjem se konvertuje u odgovarajuće acil jedinjenje opšte formule I, i/ili ukoliko je potrebno, zaštitna grupa koja je eventualno upotrebljena u gore opisanim reakcijama se odvaja i/ili ukoliko je potrebno, ovako dobijeno jedinjenje opšte formule I se razdvaja na svoje stereoizomere i/ili ukoliko je potrebno, ovako dobijeno jedinjenje opšte formule I se konvertuje u svoje soli, a naročito za farmaceutsku primenu u svoje fiziološki prihvatljive soli.
34.Postupak prema zahtevu 33, naznačen time što se jedinjenje formule III dobija postupkom prema zahtevu 29 ili 30.
35.Jedinjenje opšte formule IV u kojoj Hal označava hlor, brom ili jod i R1 označava vodonik, fluor, hlor, brom, cijano, metil, etil, izopropil, difluormetil, trifluormetil, etinil, prop-1 -in-1-il, but-1 -in-1 -ii, hidroksi, metoksi, etoksi, difluorometoksi, ciklopropiloksi, ciklobutiloksi, ciklopentiloksi ili cikloheksiloksi; i R2 označava vodonik ili metil; R3 je izabrano između sledećih: trimetilsililetil, etinil, 2-hidroksiprop-2-iletinil, 2-metoksiprop-2-iletinil, 3-hidroksi-1 -propin-1-ii, 3-metoksi-1-propin-1-il, ciklopropiloksi, ciklobutiloksi, ciklopentiloksi, cikloheksiloksi, tetrahidrofuran-3-iloksi, tetrahidropiran-4-iloksi, piperidin-4-iloksi, N- metilpiperidin-4-iloksi i acetilpiperidin-4-iloksi; i R4 označava vodonik ili fluor; i R5 označava vodonik ili fluor.
36.Jedinjenje formule IV prema zahtevu 35, naznačeno formulom IV pri čemu Hal označava hlor, brom ili jod i radikali R1, R2, R3, R4 i R5 su isti kao što je definisano u zahtevu 35.
37.Jedinjenje opšte formule II u kojoj R' označava H, C1-4-alkil, (C1-18-alkil)karbonil, (C1-18- alkiljoksikarbonil, arilkarbonil ili aril-(C1-3-alkil)-karbonilI pri čemu alkil ili aril grupe mogu biti jednostruko ili višestruko supstituisane sa halogenom; R8c, R8d su nezavisno jedan od drugog izabrani iz grupe sledećih: vodonik, (C1-18-alkil)karbonil, (C1-18-alkiljoksikarbonil, arilkarbonil i aril-(C1-3-alkil)-karbonil, ili označava benzil grupu ili RaRbRcSi grupu ili ketal ili acetal grupu, pri čemu dve susedne grupe R8a, R8b, R8c, R8d mogu uvek obrazovati cikličnu ketal ili acetal grupu ili 1,2-di(C1-3-alkoksi)-1,2-di(C1-3-alkil)-etilenski most, pri čemu gore navedeni etilenski most obrazuje supstituisani dioksanski prsten zajedno sa dva atoma kiseonika i dva pripadajuća atoma ugljenika piranoznog prstena, i alkil, aril i/ili benzil grupe mogu biti jednostruko ili višestruko supstituisane sa halogenom ili C1-3- alkoksi, a benzil grupe mogu takođe biti supstituisane sa di-(C1-3- alkiljamino grupom; i Ra, Rb, Rc nezavisno jedan od drugog označavaju C1-4-alkil, aril ili aril-C1-3- alkil, pri čemu alkil ili aril grupe mogu biti jednostruko ili višestruko supstituisane sa halogenom; pri čemu se pod aril grupama koje se pominju u definiciji gore navedenih grupa podrazumevaju fenil ili naftil grupe, a prvenstveno fenil grupe;
38. Derivati benzola supstituisani glukopiranozilom opšte formule I u kojoj su R1 do R5 definisani isto kao u jednom ili više zahteva 1 do 21, i R6 , R7a, R7b, R7c nezavisno jedan od drugog imaju značenja koja su izabrana između sledećih: (C1-18-alkil)karbonil, (C1-18-alkiljoksikarbonil, arilkarbonil i aril-(C1-3-alkil)karbonil, L2 su nezavisno jedan od drugog izabrani između sledećih: fluor, hlor, brom, jod, C1-3-alkil, difluorometil, trifluorometil, C1-3-alkoksi, difluorometoksi, trifluorometoksi i cijano; i pod aril grupama koje su pomenute u definiciji gore navedenih grupa se podrazumevaju fenil ili naftil grupe koje mogu biti jednostruko ili dvostruko supstituisane nezavisno jedna od druge sa identičnim ili različitim grupama L2; i pri čemu, osim ukoliko nije drugačije navedeno, gore navedene alkil grupe mogu biti linearne ili razgranate, njihovi tautomeri, njihovi stereoizomeri, njihove smeše i njihove soli.
39.Derivati benzola supstituisani glukopiranozilom prema zahtevu 38, naznačeni formulom 1.2. u kojoj su R1 do R5 i R6, R7a, R7b, R7c definisani isto kao u zahtevu 38.
40.Derivati benzola supstituisani glukopiranozilom prema zahtevu 38, naznačeni formulom 1.2c u kojoj su R1 do R5 i R6, R7a, R7b, R7c definisani isto kao u zahtevu 38.
41.Lek koji sadrži jedinjenje prema jednom ili više zahteva 1 do 21 ili fiziološki prihvatljivu so takvog jedinjenja, kao i najmanje jednu aktivnu supstancu koja je izabrana iz grupe antidijabetika, eventualno zajedno sa jednim ili više inertnih nosača i/ili razređivača.
42.Lek, koji sadrži jedinjenje prema jednom ili više zahteva 1 do 21 ili fiziološki prihvatljivu so takvog jedinjenja, kao i najmanje jednu aktivnu materiju koja je izabrana iz grupe sledećih: inhibitori proteina tirozinfosfataza 1, supstance koje utiču na nekontrolisanu produkciju glukoze u jetri, kao što su npr. inhibitori glukoze-6-fosfataze, ili fruktoze-1,6-bisfosfataze, glikogen fosforilaze, antagonisti glukagonskog receptora i inhibitori fosfoenol piruvat karboksikinaze, glikogen sintaze kinaze ili piruvat dehidrokinaze, agensi za smanjenje količine lipida, kao što su na primer, inhibitori HMG-CoA-reduktaze, fibrati, nikotinska kiselina i njeni derivati, PPAR-alfa agonisti, PPAR-delta agonisti, ACAT inhibitori ili inhibitori resorpcije holesterola, supstance koje vezuju žučne kiseline, inhibitori transporta ilijačnih žučnih kiselina, jedinjenja koja povećavaju količinu HDL, kao što su inhibitori CETP ili regulatori ABC1 ili aktivne supstance za lečenje gojaznosti, kao što su sibutramin ili tetrahidrolipstatin, deksfenfluramin, aksokin, antagonisti kanabinoidnih receptora 1, antagonisti MCH-1 receptora, agonisti MC4 receptora, NPY5 ili NPY2 antagonisti ili 33- agonisti i agonisti 5HT2c receptora, eventualno zajedno sa jednim ili više inertnih nosača i/ili razređivača.
43.Lek koji sadrži jedinjenje prema jednom ili više zahteva 1 do 21 ili fiziološki prihvatljivu so takvog jedinjenja, kao i najmanje jednu aktivnu supstancu koja je izabrana između lekova koji utiču na visoki krvni pritisak, hroničnu srčanu insuficijenciju ili aterosklerozu, kao što su npr. A-ll antagonisti ili ACE inhibitori, ECE-inhibitori, diuretici, β-blokatori, Ca-antagonisti, antihipertenzivi sa centralnim dejstvom, antagonisti alfa-2-adrenergenskih receptora, inhibitori neutralne endopeptidaze i inhibitori agregacije trombocita ili njihove kombinacije, eventualno zajedno sa jednim ili više inertnih nosača i/ili razređivača.
44.Lek prema zahtevu 43, naznačen time što je aktivna supstanca izabrana između antagonista receptora angiotenzina II, koji su izabrani između sledećih: kandesartan cileksetil, kalijum losartan, eprosartan mesilat, valsartan, telmisartan, irbesartan, EXP- 3174, L-158809, EXP-3312, olmesartan, medoksomil, tazosartan, KT-3-671, GA-0113, RU- 64276, EMD-90423, BR- 9701.
45.Lek koji sadrži jedinjenje prema jednom ili više zahteva 1 do 21 ili fiziološki prihvatljivu so takvog jedinjenja, kao i najmanje jednu aktivnu supstancu koja je izabrana između inhibitora sinteze mokraćne kiseline i urikosurika, eventualno zajedno sa jednim ili više inertnih nosača i/ili razređivača.
46.Lek koji sadrži jedinjenje prema jednom ili više zahteva 1 do 21 ili fiziološki prihvatljivu so takvog jedinjenja, kao i najmanje jednu aktivnu supstancu koja je izabrana između antagonista GABA-receptora, blokatora Na-kanala, topiramata, inhibitora protein-kinaze C, inhibitora krajnjih produkata uznapredovale glikozilacije i inhibitora aldoze reduktaze, eventualno zajedno sa jednim ili više inertnih nosača i/ili razređivača.
47.Lek prema jednom od zahteva 41 do 46, naznačen time, što se jedinjenje prema pronalasku ili njegova fiziološki prihvatljiva so i dodatna aktivna supstanca koja treba da se kombinuje sa njim nalaze zajedno u jednom farmaceutskom obliku ili odvojeno u dva identična ili različita farmaceutska oblika. i R1 do R5 su definisani isto kao u jednom ili više zahteva 1 i 4 do 14.
MEP-2012-72A 2004-03-16 2005-03-11 Derivati benzola supstituisani glukopiranozilom, ljekovi koji sadrže navedena jedinjenja, njihova primjena i njihov postupak proizvodnje ME01422B (me)

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NO335264B1 (no) 2014-10-27
IL177043A (en) 2013-03-24
WO2005092877A8 (de) 2006-01-26
KR20060133021A (ko) 2006-12-22
CY2014042I2 (el) 2015-12-09
BRPI0508830A (pt) 2007-08-14
PT1730131E (pt) 2012-06-15
US20090023913A1 (en) 2009-01-22
CN103450129B (zh) 2015-08-12
LU92555I2 (fr) 2014-11-24
BRPI0508830B8 (pt) 2021-05-25
HK1188775A1 (zh) 2014-05-16
KR20120007088A (ko) 2012-01-19
US20110178033A1 (en) 2011-07-21
ATE557013T1 (de) 2012-05-15
FR14C0074I1 (me) 2014-10-31
KR101174726B1 (ko) 2012-08-17
IL218714A0 (en) 2012-05-31
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NO20140127L (no) 2006-12-13
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