| Company Name: |
J & K SCIENTIFIC LTD.
|
| Tel: |
010-82848833 400-666-7788 |
| Email: |
jkinfo@jkchemical.com |
| Products Intro: |
Product Name:Alatrofloxacin Mesylate
CAS:146961-77-5
Package:100Mg,10Mg
|
| Company Name: |
Energy Chemical
|
| Tel: |
021-58432009 400-005-6266 |
| Email: |
marketing1@energy-chemical.com |
| Products Intro: |
Product Name:Alatrofloxacin Mesylate
CAS:146961-77-5
Purity:NULL Package:100mg;10mg;25mg;50mg;5mg Remarks:NULL
|
|
| | Alatrofloxacin Mesylate Basic information |
| Product Name: | Alatrofloxacin Mesylate | | Synonyms: | Alatrofloxacin Mesylate;L-Alanyl-N-[(1α,5α,6α)-3-[6-carboxy-8-(2,4-difluorophenyl)-3-fluoro-5,8-dihydro-5-oxo-1,8-naphthyridin-2-yl]-3-azabicyclo[3.1.0]hex-6-yl]-L-alaninaMide Mesylate;L-Alanyl-N-[(1α,5α,6α)-3-[6-carboxy-8-(2,4-difluorophenyl)-3-fluoro-5,8-dihydro-5-oxo-1,8-naphthyridin-2-yl]-3-azabicyclo[3.1.0]hex-6-yl]-L-alaninaMide Methanesulfonate;7-[(1S,5R)-6-[[(2S)-2-[[(2S)-2-aminopropanoyl]amino]propanoyl]amino]-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid | | CAS: | 146961-77-5 | | MF: | C27H29F3N6O8S | | MW: | 654.62 | | EINECS: | | | Product Categories: | Amines, Chiral Reagents, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals;Pharmaceuticals;Amines;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals | | Mol File: | 146961-77-5.mol |  |
| | Alatrofloxacin Mesylate Chemical Properties |
| Melting point | >225°C (dec.) | | storage temp. | Refrigerator | | solubility | DMSO (Slightly), Methanol (Slightly), Water (Slightly) | | form | Solid | | color | White to Off-White |
| | Alatrofloxacin Mesylate Usage And Synthesis |
| Chemical Properties | White Solid | | Originator | Alatrofloxacin
mesylate,Pfizer | | Uses | Alatrofloxacin Mesylate is the parental prodrug of Trovafloxacin (T893000), on phagocytic, anti-inflammatory and immunomodulation events of human THP-1 monocytes. | | Manufacturing Process | The dipolar cycloaddition of ethyldiazoacetate to the protected dihydropyrrole
(with carbobenzyloxy (CBZ) protecting group) gives the fused pyrrazolidine-
(CBZ-3-ethylperoxy-1,3a,4,5,6,6a-hexahydro-pyrrolo{3,4-c}pyrazole).
Pyrolysis results in loss of nitrogen and formation of the cyclopyrrolidine ring.
The ester is then saponified to the corresponding carboxylic acid (CBZ-6-azabicyclo[
3.1.0]hexene-3-carboxylic acid).This acid undergoes a version of the Curtius rearrangement when treated with diphenylphosphinous azide to afford
transient isocyanate. That reactive function adds tert-butanol from the
reaction medium to afford the product as its butoxycarbonyl (BOC) derivative.
CBZ-protecting group is removed by catalytic hydrogenation on Pd to afford
the BOC-protected secondary amine - BOC-6-aza-bicyclo[3.1.0]hex-3-ylamine.
In a standard quinolone reaction, this amine is then used to displace the more
reactive fluorine at 7-position in the quinolone - 1-(2,4 difluoro-phenyl)-6,7-
difluoro-4-oxo-1,4-dihydro[1,8]naphthylridine-3-carboxylic acid ethyl ester.
Treatment of the displacement product with hydrogen chloride cleaves the
BOC protecting group to afford the antibiotic trovafloxacin. The peptide-like
alanylalanylamide derivative, alatrofloxacin can in principle be prepared by
reaction of the ester precursor of trovafloxacin with alanylalanine followed by
saponification and treatment by methane sulphonic acid (mesylate). | | Brand name | Trovan (Pfizer). | | Therapeutic Function | Antibacterial |
| | Alatrofloxacin Mesylate Preparation Products And Raw materials |
|