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Levosimendan
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Synonyms:
(R)-Simendan, (-)-OR 1259
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ATC:
C01CX08
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Use:
Lorem
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:280.29 g/mol
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CAS-RN:141505-33-1
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InChI Key:WHXMKTBCFHIYNQ-SECBINFHSA-N
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InChI:InChI=1S/C14H12N6O/c1-9-6-13(21)19-20-14(9)10-2-4-11(5-3-10)17-18-12(7-15)8-16/h2-5,9,17H,6H2,1H3,(H,19,21)/t9-/m1/s1
Derivatives
racemate
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Formula:
C14H12N6O
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MW:280.29 g/mol
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CAS-RN:131741-08-7
Substances Referenced in Synthesis Path
CAS-RN |
Formula |
Chemical Name |
CAS Index Name |
5473-15-4 |
C12H13NO4 |
4-(4-acetamidophenyl)-4-oxobutanoic acid |
Benzenebutanoic acid, 4-(acetylamino)-γ-oxo- |
103-84-4 |
C8H9NO |
acetanilide |
Acetamide, N-phenyl- |
|
C19H26N2O4 |
β-[4-(acetylamino)benzoyl]-1-piperidinebutanoic acid methyl ester |
|
120757-16-6 |
C14H15NO4 |
4-(acetylamino)-β-methylene-γ-oxobenzenebutanoic acid methyl ester |
|
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 |
EU |
Lorem |
Lorem
|
|
(wfm = withdrawn from market)
References
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a racemate resolution of III:
- EP 999 999 (SmithKline & French; 14.1.1987; GB-prior. 5.7.1985).
- WO 9 999 999 (Orion; appl. 3.1.1992; GB-prior. 3.1.1991).
- WO 9 999 999 (Orion; appl. 27.3.1997; GB-prior. 27.3.1996).
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treatment of III with malononitrile:
- GB 9 999 999 (Orion; appl. 26.1.1990; GB-prior. 11.2.1989).
- US 9 999 999 (Orion; 28.3.1991; GB-prior. 11.2.1989).
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b enantioselective route:
- Baine, N. H. et al.: J. Org. Chem. (JOCEAH) 56, 1963 (1991).
- EP 999 999 (Lafon Lab.; 24.1.1985; F-prior. 14.10.1983).
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preparation of optically active 3-aroylbutyric acid esters:
- JP 99 999 999 (Mitsubishi Rayon Co.; 11.6.1996; J-prior. 28.11.1994).
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(R)-(-)-2-chloropropionyl chloride:
- Brown, H. C.: J. Am. Chem. Soc. (JACSAT) 60, 1325 (1938).
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preparation of III:
- Burpitt, B. E. et al.: J. Heterocycl. Chem. (JHTCAD) 25, 6, 1689 (1988).
- US 9 999 999 (Ross; Curran; 17.7.1973; USA-prior. 8.6.1971).
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alternative preparation of III:
- Zhao, D. et al.: Dier Junyi Daxue Xuebao (DJXUE5) 23, 2, 215 (2002).
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formulations for parenteral administration:
- WO 9999 999999 (Abbott Lab.; 10.7.2008; appl. 12.12.2007; USA-prior. 28.12.2006).
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use in the treatment of motor neuron diseases (e.g. ALS):
- WO 2016 059287 (Orion Corp.; 21.4.2016; appl. 14.10.2015; FI-prior. 15.10.2014).