HRP20210502T1 - Triterpenoidi modificirani na c-3 i c-17 kao inhibitori hiv-1 - Google Patents

Triterpenoidi modificirani na c-3 i c-17 kao inhibitori hiv-1 Download PDF

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HRP20210502T1
HRP20210502T1 HRP20210502TT HRP20210502T HRP20210502T1 HR P20210502 T1 HRP20210502 T1 HR P20210502T1 HR P20210502T T HRP20210502T T HR P20210502TT HR P20210502 T HRP20210502 T HR P20210502T HR P20210502 T1 HRP20210502 T1 HR P20210502T1
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alkyl
group
substituted
heteroaryl
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Jie Chen
Yan Chen
Ira B. Dicker
Richard A. Hartz
Nicholas A Meanwell
Alicia Regueiro-Ren
Sing-Yuen Sit
Ny Sin
Jacob Swidorski
Brian Lee Venables
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VIIV Healthcare UK (No.5) Limited
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    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
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    • C07—ORGANIC CHEMISTRY
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    • C12N9/506—Proteinases, e.g. Endopeptidases (3.4.21-3.4.25) derived from viruses derived from RNA viruses
    • 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
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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
    • C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D401/12—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 linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/52—Ortho- or ortho- and peri-condensed systems containing five condensed rings
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    • C12N2740/00—Reverse transcribing RNA viruses
    • C12N2740/00011—Details
    • C12N2740/10011—Retroviridae
    • C12N2740/16011—Human Immunodeficiency Virus, HIV
    • C12N2740/16211—Human Immunodeficiency Virus, HIV concerning HIV gagpol
    • C12N2740/16222—New viral proteins or individual genes, new structural or functional aspects of known viral proteins or genes

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Claims (17)

1. Spoj Formule I, uključujući njegove farmaceutski prihvatljive soli: [image] , naznačen time što: R1 je izopropenil ili izopropil; A je -C1-6 alkil-OR0; gdje je R0 heteroaril-Q0; Q0 se bira iz skupine koju čine -H, -CN, -C1-6 alkil, -COOH, -Ph, -OC1-6 alkil, -halogen, -CF3, Y se bira iz skupine koju čine -COOR2, -C(O)NR2SO2R3, -C(O)NHSO2NR2R2, -SO2NR2C(O)R2, -tetrazol, te -CONHOH, gdje n = 1-6; R2 je -H, -C1-6 alkil, -C1-6 alkil supstituiran alkilom ili -C1-6 alkil supstituiran arilom; W je odsutan, ili je -CH2- ili -CO-; R3 je -H, -C1-6 alkil ili -C1-6 alkil supstituiran alkilom; R4 se bira iz skupine koju čine -H, -C1-6 alkil, -C1-6 alkil-C3-6 cikloalkil, -C1-6 alkil supstituiran s -C1-6, -C1-6 alkil-Q1, -C1-6 alkil-C3-6 cikloalkil-Q1, aril, heteroaril, supstituirani heteroaril, -COR6, -SO2R7, -SO2NR2R2, te [image] , [image] , gdje se G bira iz skupine koju čine -O-, -SO2- i -NR12-; gdje se Q1 bira iz skupine koju čine -C1-6 alkil, -C1-6 fluoralkil, heteroaril, supstituirani heteroaril, halogen, -CF3, -OR2, -COOR2, -NR8R9, -CONR8R9 i -SO2R7; R5 se bira iz skupine koju čine -H, -C1-6 alkil, -C3-6 cikloalkil, -alkil supstituiran s C1-6 alkilom, -C1-6 alkil-NR8R9, -COR3, -SO2R7 i -SO2NR2R2; uz uvjet da R4 ili R5 nije -COR6 kada je W -CO-; uz dodatni uvjet da se samo jedan od R4 ili R5 bira iz skupine koju čine -COR6, -COCOR6, -SO2R7 i -SO2NR2R2; R6 se bira iz skupine koju čine -H, -C1-6 alkil, -alkil supstituiran s C1-6 alkilom, -C3-6 cikloalkil, -C3-6 supstituirani-cikloalkil-Q2, -C1-6 alkil-Q2, -alkil supstituiran s C1-6 alkilom-Q2, -C3-6 cikloalkil-Q2, aril-Q2, -NR13R14, te -OR15; gdje se Q2 bira iz skupine koju čine aril, heteroaril, supstituirani heteroaril, -OR2, -COOR2, -NR8R9, SO2R7, -CONHSO2R3, te -CONHSO2NR2R2; R7 se bira iz skupine koju čine -H, -C1-6 alkil, -alkil supstituiran s C1-6, -C3-6 cikloalkil, -CF3, aril, te heteroaril; R8 i R9 se neovisno bira iz skupine koju čine -H, -C1-6 alkil, -alkil supstituiran s C1-6, aril, heteroaril, supstituirani aril, supstituirani heteroaril, -C1-6 alkil-Q2, te -COOR3, ili se R8 i R9 uzima zajedno sa susjednim N kako bi tvorili prsten kojeg se bira iz skupine koju čine: [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] i [image] ; M se bira iz skupine koju čine -R15, -SO2R2, -SO2NR2R2, -OH i -NR2R12; V se bira iz skupine koju čine -CR10R11-, -SO2-, -O- i -NR12-; uz uvjet da samo jedan od R8 ili R9 može biti -COOR3; R10 i R11 se neovisno bira iz skupine koju čine -H, -C1-6 alkil, -alkil supstituiran s C1-6 i -C3-6 cikloalkil; R12 se bira iz skupine koju čine -H, -C1-6 alkil, -C1-6 alkil supstituiran alkilom, -CONR2R2, -SO2R3, te -SO2NR2R2; R13 i R14 se neovisno bira iz skupine koju čine -H, -C1-6 alkil, -C3-6 cikloalkil, -alkil supstituiran s C1-6, -C1-6 alkil-Q3, -C1-6 alkil-C3-6 cikloalkil-Q3, te alkil supstituiran s C1-6-Q3; Q3 se bira iz skupine koju čine heteroaril, supstituirani heteroaril, -NR2R12, -CONR2R2, -COOR2, -OR2, te -SO2R3; R15 se bira iz skupine koju čine -C1-6 alkil, -C3-6 cikloalkil, -alkil supstituiran s C1-6, -C1-6 alkil-Q3, -C1-6 alkil-C3-6 cikloalkil-Q3 i -alkil supstituiran s C1-6-Q3; R16 se bira iz skupine koju čine -H, -C1-6 alkil, -NR2R2, te -COOR2; uz uvjet da kada je V -NR12-; R16 nije -NR2R2; i R17 se bira iz skupine koju čine -H, -C1-6 alkil, -COOR3, te aril.
2. Spoj u skladu s patentnim zahtjevom 1, naznačen time što se u skupini R0 heteroarilni ostatak bira iz skupine koju čine: [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , te [image] .
3. Spoj u skladu s patentnim zahtjevom 2, naznačen time što je R1 izopropenil.
4. Spoj u skladu s patentnim zahtjevom 3, naznačen time što je Y -COOR2.
5. Spoj u skladu s patentnim zahtjevom 4, naznačen time što je R2 -H.
6. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je R4 -C1-6 alkil-Q1.
7. Spoj u skladu s patentnim zahtjevom 6, naznačen time što je Q1 -NR8R9.
8. Spoj u skladu s patentnim zahtjevom 7, naznačen time što kada se R8 i R9 uzima zajedno sa susjednim -N kako bi tvorili prsten, prsten se bira iz skupine koju čine: [image] i [image] .
9. Spoj u skladu s patentnim zahtjevom 8, naznačen time što se svakog od R7 i R16 bira iz skupine koju čine -H i -C1-6 alkil.
10. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je Q0 -CN.
11. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je R1 izopropenil, u skupini R0 "heteroarilni" ostatak se bira iz skupine koju čine: [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , te [image] ; Y je -COOH, R4 je -C1-6 alkil-Q1, Q1 je -NR8R9, a R8 i R9 se uzima zajedno sa susjednim -N kako bi tvorili prsten kojeg se bira iz skupine koju čine: [image] i [image] .
12. Spoj u skladu s patentnim zahtjevom 1, uključujući njegove farmaceutski prihvatljive soli, naznačen time što ga se bira iz skupine koju čine: [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] i [image] .
13. Spoj u skladu s patentnim zahtjevom 1, uključujući njegove farmaceutski prihvatljive soli, naznačen time što ga se bira iz skupine koju čine: [image] , [image] , [image] , te [image] .
14. Spoj, uključujući njegove farmaceutski prihvatljive soli u skladu s patentnim zahtjevom 13, naznačen time što je: [image] .
15. Pripravak, naznačen time što sadrži količinu koja ublažava HIV jednog ili više spojeva u skladu s patentnim zahtjevom 1-14, zajedno s jednim ili više farmaceutski prihvatljivih nosača, pomoćnih sredstava i/ili razrjeđivača.
16. Spoj, ili njegova farmaceutski prihvatljiva sol, u skladu s patentnim zahtjevima 1-14, naznačen time što je namijenjen upotrebi u terapiji.
17. Spoj, ili njegova farmaceutski prihvatljiva sol, u skladu s patentnim zahtjevima 1-14, naznačen time što je namijenjen upotrebi u liječenju sisavca zaraženog virusom HIV.
HRP20210502TT 2016-02-04 2021-03-29 Triterpenoidi modificirani na c-3 i c-17 kao inhibitori hiv-1 HRP20210502T1 (hr)

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US201662291298P 2016-02-04 2016-02-04
EP17704093.8A EP3411381B1 (en) 2016-02-04 2017-02-02 C-3 and c-17 modified triterpenoids as hiv-1 inhibitors
PCT/IB2017/050568 WO2017134596A1 (en) 2016-02-04 2017-02-02 C-3 and c-17 modified triterpenoids as hiv-1 inhibitors

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KR (1) KR20180105229A (hr)
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