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DK3041827T3 - 1,2,4-oxadiazolderivater som immunmodulatorer - Google Patents

1,2,4-oxadiazolderivater som immunmodulatorer Download PDF

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Publication number
DK3041827T3
DK3041827T3 DK14790320.7T DK14790320T DK3041827T3 DK 3041827 T3 DK3041827 T3 DK 3041827T3 DK 14790320 T DK14790320 T DK 14790320T DK 3041827 T3 DK3041827 T3 DK 3041827T3
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Prior art keywords
compound
pharmaceutically acceptable
acceptable salt
following structure
amino acid
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DK14790320.7T
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English (en)
Inventor
Pottayil Govindan Nair Sasikumar
Muralidhara Ramachandra
Seetharamaiah Setty Sudarshan Naremaddepalli
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Aurigene Discovery Tech Ltd
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    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
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Claims (48)

1. Forbindelse med formel (I)
hvor, Q er S eller O; Ri repræsenterer en sidekæde af en aminosyrerest udvalgt fra Ser og Thr, eventuelt substitueret med alkyl eller acyl; R2 er hydrogen eller -CO-Aaa; Aaa er en aminosyrerest udvalgt fra Thr og Ser; hvor en C-terminus deraf er en fri terminus, er amideret eller er esterificeret; R3 repræsenterer en sidekæde af en aminosyrerest udvalgt fra Asn, Asp, Gin og Glu; -----er en eventuel binding; R4 og R5 uafhængigt er hydrogen eller fraværende; R6 er hydrogen, alkyl eller acyl; eller et farmaceutisk acceptabelt salt deraf.
2. Forbindelse ifølge krav 1, hvor Q er O.
3. Forbindelse ifølge krav 1, hvor Re er H.
4. Forbindelse ifølge krav 1, hvor Re er -C(0)CH3, -C(0)CH2CH3, -C(0)(CH2)2CH3, -C(0)(CH2)3CH3, -C(0)(CH2)4CH3 eller -C(0)(CH2)5CH3.
5. Forbindelse ifølge krav 1, hvor R2 er -CO-Aaa.
6. Forbindelse ifølge krav 1, hvor forbindelsen med formlen (I) er en forbindelse med formlen (IA):
eller et farmaceutisk acceptabelt salt deraf; hvor, Ri repræsenterer en sidekæde af en aminosyrerest udvalgt fra Ser og Thr, eventuelt substitueret med alkyl eller acyl; R3 repræsenterer en sidekæde af en aminosyrerest udvalgt fra Asn, Asp, Gin og Glu; og Aaa er en aminosyrerest udvalgt fra Thr og Ser; hvor C-terminus deraf er en fri terminus, er amideret eller er esterificeret.
7. Forbindelse ifølge krav 1, hvor Aaa er en aminosyrerest udvalgt fra Thr og Ser; hvor C-terminus er en fri terminus.
8. Forbindelse ifølge krav 1, hvor forbindelsen med formlen (I) er en forbindelse med formlen (IB):
eller et farmaceutisk acceptabelt salt deraf; hvor, Ri repræsenterer en sidekæde af en aminosyrerest udvalgt fra Ser og Thr, eventuelt substitueret med alkyl eller acyl; og R3 repræsenterer en sidekæde af en aminosyrerest udvalgt fra Asn, Asp, Gin og Glu.
9. Forbindelse ifølge krav 1, hvor: Ri repræsenterer en sidekæde af en aminosyrerest udvalgt fra Ser og Thr.
10. Forbindelse ifølge krav 1, hvor Ri er substitueret med Ci-5-alkyl.
11. Forbindelse ifølge krav 1, hvor R3 repræsenterer en sidekæde af en aminosyrerest udvalgt fra Asn og Glu.
12. Forbindelse ifølge krav 1, hvor: Ri repræsenterer en sidekæde af en aminosyrerest udvalgt fra Ser og Thr; R2 er -CO-Aaa; Aaa er en aminosyrerest udvalgt fra Thr og Ser; hvor C-terminus er en fri terminus; R3 repræsenterer en sidekæde af en aminosyrerest udvalgt fra Asn og Glu.
13. Forbindelse ifølge krav 1, hvor Ri repræsenterer en sidekæde af en aminosyrerest Ser.
14. Forbindelse ifølge krav 1, hvor Ri repræsenterer en sidekæde af en aminosyrerest Thr.
15. Forbindelse ifølge krav 1, hvor Aaa er Ser.
16. Forbindelse ifølge krav 1, hvor Aaa er Thr.
17. Forbindelse ifølge krav 1, hvor R3 repræsenterer en sidekæde af en aminosyrerest Asn.
18. Forbindelse ifølge krav 1, hvor R3 repræsenterer en sidekæde af en aminosyrerest Asp.
19. Forbindelse ifølge krav 1, hvor R3 repræsenterer en sidekæde af en aminosyrerest Gin.
20. Forbindelse ifølge krav 1, hvor R3 repræsenterer en sidekæde af en aminosyrerest Glu.
21. Forbindelse ifølge krav 1, hvor R2 er H.
22. Forbindelse ifølge krav 1, der har følgende struktur:
eller et farmaceutisk acceptabelt salt deraf.
23. Forbindelse ifølge krav 1, der har følgende struktur:
eller et farmaceutisk acceptabelt salt deraf.
24. Forbindelse ifølge krav 1, der har følgende struktur:
eller et farmaceutisk acceptabelt salt deraf.
25. Forbindelse ifølge krav 1, der har følgende struktur:
eller et farmaceutisk acceptabelt salt deraf.
26. Forbindelse ifølge krav 1, der har følgende struktur:
eller et farmaceutisk acceptabelt salt deraf.
27. Forbindelse ifølge krav 1, der har følgende struktur:
eller et farmaceutisk acceptabelt salt deraf.
28. Forbindelse ifølge krav 1, der har følgende struktur:
eller et farmaceutisk acceptabelt salt deraf.
29. Forbindelse ifølge krav 1, der har følgende struktur:
eller et farmaceutisk acceptabelt salt deraf.
30. Forbindelse ifølge krav 1, der har følgende struktur:
eller et farmaceutisk acceptabelt salt deraf.
31. Forbindelse ifølge krav 1, der har følgende struktur:
eller et farmaceutisk acceptabelt salt deraf.
32. Forbindelse ifølge krav 1, der har følgende struktur:
eller et farmaceutisk acceptabelt salt deraf.
33. Forbindelse ifølge krav 1, der har følgende struktur:
eller et farmaceutisk acceptabelt salt deraf.
34. Forbindelse ifølge krav 1, der har følgende struktur:
eller et farmaceutisk acceptabelt salt deraf.
35. Forbindelse ifølge krav 1, der har følgende struktur:
eller et farmaceutisk acceptabelt salt deraf.
36. Forbindelse ifølge krav 1, der har følgende struktur:
eller et farmaceutisk acceptabelt salt deraf.
37. Forbindelse ifølge krav 1, der har følgende struktur:
eller et farmaceutisk acceptabelt salt deraf.
38. Forbindelse ifølge krav 1, der har følgende struktur:
eller et farmaceutisk acceptabelt salt deraf.
39. Forbindelse ifølge krav 1, der har følgende struktur:
eller et farmaceutisk acceptabelt salt deraf.
40. Forbindelse ifølge krav 1, der har følgende struktur:
eller et farmaceutisk acceptabelt salt deraf.
41. Forbindelse ifølge krav 1, der har følgende struktur:
eller et farmaceutisk acceptabelt salt deraf.
42. Forbindelse ifølge krav 1, der har følgende struktur:
eller et farmaceutisk acceptabelt salt deraf.
43. Forbindelse ifølge krav 1, der har følgende struktur:
eller et farmaceutisk acceptabelt salt deraf.
44. Forbindelse ifølge krav 1, der har følgende struktur:
eller et farmaceutisk acceptabelt salt deraf.
45. Forbindelse ifølge krav 1, der har følgende struktur:
eller et farmaceutisk acceptabelt salt deraf.
46. Forbindelse ifølge krav 1, der har følgende struktur:
eller et farmaceutisk acceptabelt salt deraf.
47. Farmaceutisk sammensætning, der omfatter en farmaceutisk acceptabel bærer eller excipiens og mindst én forbindelse ifølge et hvilket som helst af kravene 1-46 eller et farmaceutisk acceptabelt salt deraf.
48. Farmaceutisk sammensætning ifølge krav 47, der endvidere omfatter mindst ét middel af et anticancermiddel, et kemoterapimiddel og en antiproliferativ forbindelse.
DK14790320.7T 2013-09-06 2014-09-05 1,2,4-oxadiazolderivater som immunmodulatorer DK3041827T3 (da)

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IN4011CH2013 2013-09-06
PCT/IB2014/064279 WO2015033299A1 (en) 2013-09-06 2014-09-05 1,2,4-oxadiazole derivatives as immunomodulators

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