455264-30-9

Usage

Uses

Used in Pharmaceutical Research:
(S)-ethyl 3-(4-(2,7-naphthyridin-1-ylaMino)phenyl)-2-(2-broMo-3-oxospiro[3.5]non-1-en-1-ylaMino)propanoate is used as a potential candidate in pharmaceutical research for the development of new medications. The presence of the naphthyridine ring, which is commonly found in antibiotics, suggests that (S)-ethyl 3-(4-(2,7-naphthyridin-1-ylaMino)phenyl)-2-(2-broMo-3-oxospiro[3.5]non-1-en-1-ylaMino)propanoate could be explored for its antibacterial properties.
Used in Chemical Synthesis:
In the chemical industry, (S)-ethyl 3-(4-(2,7-naphthyridin-1-ylaMino)phenyl)-2-(2-broMo-3-oxospiro[3.5]non-1-en-1-ylaMino)propanoate can be used as a building block or intermediate in the synthesis of more complex molecules with specific applications in various fields, such as materials science, agrochemicals, or pharmaceuticals.

Upstream product

• 455264-29-6 UC⁽⁹³³⁾B₁₁₉₄ 
• 69042-30-4 1-chloro-[2,7]naphthyridine 

Downstream Products

• 455264-31-0 zaurategrast 

Relevant academic research and scientific papers

Monitoring and control of genotoxic impurity acetamide in the synthesis of zaurategrast sulfate

In this article we describe the strategy adopted to minimize the risk of acetamide presence in zaurategrast sulfate drug candidate. A risk of acetamide formation (a potential genotoxic impurity) was identified in the API formation step of the process during the early development phase. In order to keep the project development timelines unchanged and without having the appropriate analytical method ready developed, we chose to minimize the risk of acetamide impurity presence by applying an adequate chemical process design. The implementation of a workup sequence involving initially three aqueous washes was later proven to be successful when an appropriate analytical method to detect acetamide below ppm levels was available. Additionally the analytical tool gave us the opportunity to assess and fine-tune the designed process for acetamide elimination by spiking experiments. Data acquired during this evaluation showed that a single aqueous wash associated with two efficient crystallization steps were finally enough to deliver API with a content of acetamide below the level defined as the acceptance criterion.

PROCESS FOR THE PREPARATION OF PHENYLALANINE ENAMIDE DERIVATIVES

A process for the preparation of a class of phenylalanine enamide derivatives is described formula (1) wherein: Ar1 is an optionally substituted aromatic or heteroaromatic group; L2 is a linker group selected from -N(R4)- [where R4 is a hydrogen atom or an optionally substituted straight or branched C1-6alkyl group], -CON(R4)-, or -S(O)2N(R4)-; R1 is a carboxylic acid (-CO2H) or a derivative or biostere thereof; R2 is a hydrogen atom or a C1-6alkyl group; Rx, Ry and Rz which may be the same or different is each an atom or group -L1(Alk1)n(R3)v; and the salts, solvates, hydrates and N-oxides thereof; which comprises reacting a compound of formula (2): wherein: Qa is a group -N(R4)H; and the salts, solvates, hydrates and N-oxides thereof; with a compound Ar1W wherein W is a group selected from X1 (wherein X1 is a leaving atom or group), -COX2 (wherein X2 is a halogen atom or a -OH group) or -SO2 X3 (in which X3 is a halogen atom).

PHENYLALANINE ENAMIDE DERIVATIVES

Phenylalanine enamide derivatives of formula (1) are described, wherein R1is a -CH(CH3)2, -(CH2)2CH3; -CH2C(CH3)3, -CH2CH2OH, -CH2CH2OCH3, -CH2CH2OCH2CH2OH, -CH2CH2OCH2CH2OCH3, formula (A) group; and the salts, solvates and N-oxides thereof. Compounds according to the invention are potent and selective inhibitors of α4 integrins. The compounds are of use in modulating cell adhesion and in particular are of use in the prophylaxis and treatment of diseases or disorders including inflammation in which the extravasation of leukocytes plays a role and the invention extends to such a use and to the use of the compounds for the manufacture of a medicament for treating such diseases or disorders.

Phenylalanine enamide derivatives

Phenylalanine enamide derivatives of formula (1) are described: wherein R1 is a group Ar1L2Ar2Alk- in which: Ar1 is an optionally substituted aromatic or heteroaromatic group; L2 is a covalent bond or a linker atom or group; Ar2 is an optionally substituted arylene or heteroarylene group; and Alk is a chain —CH2—CH(R)13 , —CH═C(R)— or ?in which R is a carboxylic acid (—CO2H) or a derivative or biostere thereof; X is an —O— or —S— atom or —N(R2)— group in which: Rx, Ry and Rz which may be the same or different is each a hydrogen atom or an optional substituent; or Rz is an atom or group as previously defined and Rx and Ry are joined together to form an optionally substituted spiro linked cycloaliphatic or heterocycloaliphatic group; and the salts, solvates, hydrates and N-oxides thereof. The compounds are able to inhibit the binding of integrins to their ligands and are of use in the prophylaxis and treatment of immuno or inflammatory disorders or disorders involving the inappropriate growth or migration of cells.