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==Synthesis== ==Synthesis==
The chemical synthesis of milverine was identified.<ref>Paolo Masi, Angela Monopoli, Adone Carlo Saravalle, Cesare Zio, DE3002909 (1980 to Italiana Schoum Spa). </ref> The chemical synthesis of milverine was identified.<ref>Paolo Masi, Angela Monopoli, Adone Carlo Saravalle, Cesare Zio, DE3002909 (1980 to Italiana Schoum Spa). </ref>
] ]
Conjugate soft addition of benzene to cinnamic acid (1) gives 3,3-diphenylpropionic acid (2). Halogenation with thionyl chloride gives 3,3-diphenylpropionyl chloride (3). Schotten-Baumann reaction with 4-aminopyridine (Fampridine) (4) gives 3,3-diphenyl-N-(4-pyridyl)propionamide (5). The last step involves reduction of the amide bond giving milverine (6), respectively. Conjugate soft addition of benzene to cinnamic acid (1) gives 3,3-diphenylpropionic acid (2). Halogenation with thionyl chloride gives 3,3-diphenylpropionyl chloride (3). Schotten-Baumann reaction with 4-aminopyridine (Fampridine) (4) gives 3,3-diphenyl-N-(4-pyridyl)propionamide (5). The last step involves reduction of the amide bond giving milverine (6), respectively.
== References == == References ==

Revision as of 10:26, 17 December 2024

Pharmaceutical compound
Milverine
Clinical data
Other namesFenprin, Fenpyramine, Miospasm.
Identifiers
IUPAC name
  • N-(3,3-diphenylpropyl)pyridin-4-amine
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H20N2
Molar mass288.394 g·mol
3D model (JSmol)
SMILES
  • C1=CC=C(C=C1)C(CCNC2=CC=NC=C2)C3=CC=CC=C3
InChI
  • InChI=1S/C20H20N2/c1-3-7-17(8-4-1)20(18-9-5-2-6-10-18)13-16-22-19-11-14-21-15-12-19/h1-12,14-15,20H,13,16H2,(H,21,22)
  • Key:KMZHYAUKFHLFNY-UHFFFAOYSA-N

Milverine is a spasmolytic (antispasmodic) agent that was developed in the latter half of the 20th century.

The therapeutic use of fenpyramin as a platelet-antiaggregating and antithrombotic as well as vasodilating and antianginous medicine was also identified.

Synthesis

The chemical synthesis of milverine was identified.

Milverine synthesis
Milverine synthesis

Conjugate soft addition of benzene to cinnamic acid (1) gives 3,3-diphenylpropionic acid (2). Halogenation with thionyl chloride gives 3,3-diphenylpropionyl chloride (3). Schotten-Baumann reaction with 4-aminopyridine (Fampridine) (4) gives 3,3-diphenyl-N-(4-pyridyl)propionamide (5). The last step involves reduction of the amide bond giving milverine (6), respectively.

References

  1. Carpenedo F, Santi-soncin E. . Minerva Med. 1970;61(43):2417-24. PMID: 5425728.
  2. Baldi, F. et al, Curr. Ther. Res., 1984,36, 267 (pharmacol)
  3. Fossati A, Sosio A, Pellegrini R, Frigo GM, D'Angelo L, Lecchini S, Marcoli M, Caravaggi M, Crema A. Milverine: in vitro and in vivo activity on the animal and human colon. Farmaco Prat. 1986 Sep;41(9):279-89. PMID: 3770157.
  4. Rinaldo Pellegrini, Gaetano Clavenna, Piero Bellani, EP0143082 (1985 to RBS PHARMA (ROGER BELLON SCHOUM) S.p.A.).
  5. Paolo Masi, Angela Monopoli, Adone Carlo Saravalle, Cesare Zio, DE3002909 (1980 to Italiana Schoum Spa).