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Gemcitabine

  • Synonyms: dFdC, LY-188011
  • ATC: L01BC05
  • Use: Lorem  Lorem 
  • Chemical name: Lorem ipsum dolor sit amet, consetetur sadipscing elitr, sed diam
  • Formula: Lorem ipsum dolor sit amet,
  • MW:263.20 g/mol
  • CAS-RN:95058-81-4
  • InChI Key:SDUQYLNIPVEERB-UHFFFAOYSA-N
  • InChI:InChI=1S/C9H11F2N3O4/c10-​9(11)​6(16)​4(3-​15)​18-​7(9)​14-​2-​1-​5(12)​13-​8(14)​17/h1-​2,​4,​6-​7,​15-​16H,​3H2,​(H2,​12,​13,​17)

Derivatives

    monohydrochloride

  • Use:
  • Formula: Lorem ipsum dolor sit amet,
  • MW:299.66 g/mol
  • CAS-RN:122111-03-9

Substance Classes

Synthesis Path



























Substances Referenced in Synthesis Path

CAS-RN Formula Chemical Name CAS Index Name
108-24-7 C4H6O3 acetic anhydride Acetic acid, anhydride
18027-23-1 C12H23N3O2Si2 N-acetyl-N,O-bis(trimethylsilyl)cytosine Acetamide, N-(trimethylsilyl)-N-[2-[(trimethylsilyl)oxy]-4-pyrimidinyl]-
14631-20-0 C6H7N3O2 N-acetylcytosine
98-88-4 C7H5ClO benzoyl chloride Benzoyl chloride
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem

Trade Names

Country Trade Name Vendor Annotation
D Lorem Lorem
F Lorem Lorem
GB Lorem Lorem
I Lorem Lorem
USA Lorem Lorem as hydrochloride
(wfm = withdrawn from market)

Formulations

  • Loremipsumdolorsitamet,consetetursadipscing

References

    • a Hertel, L.W. et al.: J. Org. Chem. (JOCEAH) 53 (11), 2406-2409 (1988).
    •  US 9 999 999 (Eli Lilly; 2.7.1985; appl. 10.3.1983).
    •  US 9 999 999 (Eli Lilly; 8.9.1987; appl. 4.12.1984; USA-prior. 10.3.1983).
    •  US 9 999 999 (Eli Lilly; 28.2.1989; appl. 4.6.1987; USA-prior. 10.3.1984, 4.12.1984).
    •  EP 999 999 (Eli Lilly; appl. 6.3.1984; USA-prior. 10.3.1983).
    •  EP 999 999 (Eli Lilly; appl. 25.11.1985; USA-prior. 4.12.1984).
    •  US 9 999 999 (Eli Lilly; 2.6.1992; appl. 7.2.1991; USA-prior. 10.3.1983, 4.12.1984, 4.6.1987, 20.12.1988, 15.12.1989).
    • b US 9 999 999 (Eli Lilly; 23.10.1990; appl. 4.12.1989; USA-prior. 28.8.1987, 24.8.1988).
    •  US 9 999 999 (Eli Lilly; 29.6.1993; appl. 12.7.1990; USA-prior. 28.8.1987, 24.8.1988, 4.12.1989).
    •  US 9 999 999 (Eli Lilly; 10.6.1997; appl. 13.12.1994).
    •  US 9 999 999 (Eli Lilly; 15.9.1998; appl. 11.4.1997; USA-prior. 13.12.1994).
    •  EP 999 999 (Eli Lilly; appl. 22.8.1988; USA-prior. 28.8.1987).
    • c US 9 999 999 (Eli Lilly; 27.6.1995; appl. 14.4.1994).
    •  US 9 999 999 (Eli Lilly; 26.5.1998; appl. 9.12.1996; USA-prior. 13.12.1995).
    •  US 9 999 999 (Eli Lilly; 15.6.1999; appl. 22.1.1998; USA-prior. 13.12.1995, 9.12.1996).
    •  US 9 999 999 (Eli Lilly; 14.12.1999; appl. 10.12.1998; USA-prior. 13.12.1995, 9.12.1996, 22.1.1998).
    • d US 9 999 999 999 (Maikap, G.C. et al., India; 28.9.2006; IN-prior. 4.3.2005).
  • separation of α- and β-forms (anomers) of VI:

    • US 9 999 999 (Eli Lilly; 26.10.1993; appl. 22.6.1992).
  • conversion of β-2-deoxy-2,2-difluoro-d-ribofuranosyl mesylate (IX) to α-anomer by heating in acetonitrile in presence of N,N-dimethylbenzylammonium mesylate:

    • US 9 999 999 (Eli Lilly; 26.10.1993; appl. 22.6.1992).
  • by contacting (VIII) with triethylamine before mesylation at –78 °C:

    • US 9 999 999 (Eli Lilly; 28.3.1995; appl. 22.6.1992).
  • by heating without solvents to 120-130°C and subsequent fract. crystallisation:

    • US 9 999 999 999 (ScinoPharm Taiwan; 7.12.2006; appl. 24.5.2006; USA-prior. 3.6.2005).
  • enriched β-anomer formation in reaction between (IV) and (VI) by using special conditions:

    • US 9 999 999 (Eli Lilly; 6.12.1994; appl. 22.6.1992).
    • US 9 999 999 (Eli Lilly; 28.3.1995; appl. 7.4.1993; USA-prior. 22.6.1992).
    • US 9 999 999 (Eli Lilly; 13.6.1995; appl. 25.8.1993).
    • US 9 999 999 (Eli Lilly; 20.6.1995; appl. 7.4.1993; USA-prior. 22.6.1992).
    • US 9 999 999 (Eli Lilly; 14.1.1997; appl. 7.4.1993; USA-prior. 22.6.1992).
    • US 9 999 999 (Eli Lilly; 25.2.1997; appl. 17.11.1994; USA-prior. 22.6.1992, 7.4.1993).
  • use of trityl groups for protection of intermediates:

    • US 9 999 999 (Eli Lilly; 24.9.1996; appl. 3.2.1995).
    • US 9 999 999 (Eli Lilly; 4.3.1997; appl. 16.5.1996; USA-prior. 3.2.1995).
  • preparation from cytidine by oxidation to the 2-keto derivative, acetylation and direct fluorination with DAST/pyridine-HF:

    • US 9 999 999 (Eli Lilly; 27.5.1997; appl. 24.3.1995).
  • conversion of the α-form of gemcitabine to the β-form:

    • US 9 999 999 (Eli Lilly; 30.5.1995; appl. 3.1.1994; USA-prior. 1.9.1992).
  • recovery of (V) from the α-anomer of gemcitabine via 2-deoxy-2,2-difluororibopyranose:

    • US 9 999 999 (Eli Lilly; 4.9.1990; appl. 13.11.1989; USA-prior. 20.3.1989).
  • synthesis from d-glucose:

    • Fernandez, R. et al.: Tetrahedron (TETRAB) 54, 9999 (1998).
  • medical use (antitumor):

    • US 9 999 999 (Eli Lilly; 7.11.1995; appl. 26.7.1994; USA-prior. 4.12.1984, 10.10.1985, 3.3.1988, 16.8.1991, 29.7.1993).
  • oncolytic combinations for the treatment of cancer:

    • WO 9 999 999 999 (Lilly; 17.5.2001; appl. 9.11.2000; USA-prior. 11.11.1999).
  • liposomal formulations:

    • DE 99 999 999 (Unger; 30.9.1999; appl. 27.3.1998).
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