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Gemcitabine
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Synonyms:
dFdC, LY-188011
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ATC:
L01BC05
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Use:
Lorem
Lorem
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Chemical name:
Lorem ipsum dolor sit amet, consetetur sadipscing elitr, sed diam
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Formula:
Lorem ipsum dolor sit amet,
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MW:263.20 g/mol
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CAS-RN:95058-81-4
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InChI Key:SDUQYLNIPVEERB-UHFFFAOYSA-N
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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
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Use:
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Formula:
Lorem ipsum dolor sit amet,
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MW:299.66 g/mol
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CAS-RN:122111-03-9
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 |
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Lorem |
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Lorem |
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Lorem |
Lorem |
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Lorem |
Lorem |
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Lorem |
Lorem |
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Lorem |
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Lorem |
Lorem |
Trade Names
Country |
Trade Name |
Vendor |
Annotation |
D |
Lorem |
Lorem
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F |
Lorem |
Lorem
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GB |
Lorem |
Lorem
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I |
Lorem |
Lorem
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USA |
Lorem |
Lorem
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as hydrochloride |
(wfm = withdrawn from market)
Formulations
- Loremipsumdolorsitamet,consetetursadipscing
References
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- 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).
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separation of α- and β-forms (anomers) of VI:
- US 9 999 999 (Eli Lilly; 26.10.1993; appl. 22.6.1992).
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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).
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by contacting (VIII) with triethylamine before mesylation at –78 °C:
- US 9 999 999 (Eli Lilly; 28.3.1995; appl. 22.6.1992).
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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).
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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).
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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).
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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).
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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).
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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).
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synthesis from d-glucose:
- Fernandez, R. et al.: Tetrahedron (TETRAB) 54, 9999 (1998).
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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).
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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).
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liposomal formulations:
- DE 99 999 999 (Unger; 30.9.1999; appl. 27.3.1998).