195532-12-8

Basic information

• Product Name: 8-cyano-1-cyclopropyl-6-fluoro-7-[(4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• Synonyms: 195532-12-8; pradofloxacin
• CAS NO: 195532-12-8
• Molecular Formula: C₂₁H₂₁FN₄O₃
• Molecular Weight: 396.4148
• Mol File: 195532-12-8.mol

Chemical Properties

• Boiling Point: 664.525°C at 760 mmHg
• Flash Point: 355.692°C
• Density: 1.504g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.691
• CAS DataBase Reference: 8-cyano-1-cyclopropyl-6-fluoro-7-[(4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 8-cyano-1-cyclopropyl-6-fluoro-7-[(4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid(195532-12-8)
• EPA Substance Registry System: 8-cyano-1-cyclopropyl-6-fluoro-7-[(4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid(195532-12-8)

Safety Data

• Hazardous Substances Data: 195532-12-8(Hazardous Substances Data)

Upstream product

• 280-57-9 1,4-diaza-bicyclo[2.2.2]octane 
• 117528-65-1 7-chloro-8-cyano-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid 
• 151213-40-0 (1S,6S)-2,8-diazabicyclo[4.3.0]nonane 
• 117528-63-9 ethyl 2-(2,4-dichloro-3-cyano-5-fluorobenzoyl)-3-cyclopropylaminoacrylate 
• 195532-64-0 3-cyano-2,4,5-trifluoro-benzoic acid 
• 195532-67-3 Ethyl 2-(3-cyano-2,4,5-trifluoro-benzoyl)-3-dimethylamino-acrylate 
• 117528-58-2 2,4-dichloro-3-cyano-5-fluorobenzoic acid 
• 1159908-25-4 C₁₅H₁₃Cl₂FN₂O₃ 

Downstream Products

• 195532-36-6 8-Cyano-1-cyclopropyl-7-[(1S,6S)-2-((S)-alanyl)-2,8-diazabicyclo[4.3.0]nonan-8-yl]-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid hydrochloride 
• 195532-27-5 8-Cyano-1-cyclopropyl-7-[(1S,6S)-2-(3-oxo-butyl)-2,8-diazabicyclo[4.3.0]nonan-8-yl]-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid 

Relevant articles and documents

Synthesis method of pradofloxacin

The invention relates to a synthesis method of pradofloxacin. According to the method, a cheap and easy-to-obtain compound is taken as a raw material and subjected to chlorination, acylation, nucleophilic substitution, cyclization, hydrolysis and alkylation reactions, and the target product, namely, pradofloxacin, is obtained. The nucleophilic substitution target product beta-substituted amino-alpha-substituted benzoyl acrylate compound has good quality and has the purity of 98% or above and the yield of 80%-90%, and the yield is increased by 10% or above as compared with that in the prior art; the provided ester hydrolysis method and product quality are good, and the reaction yield reaches 93%-98%; organic base is used for replacing conventional inorganic base to serve as a cyclization reaction catalyst, the operation is simple, no pollution is caused, and the cost is substantially reduced; halogenated hydrocarbon is taken as an alkylation solvent, the reaction temperature is the roomtemperature, the reaction is mild and easy to operate, fewer impurities are produced in the alkylation reaction at the temperature of 20-40 DEG C as compared with those produced in the alkylation reaction at the high temperature in the prior art, the yield is high, halogenated hydrocarbon solvents are easy to recycle and reuse, pollution is greatly reduced, and the synthesis method is environmentally friendly.

PROCESS FOR PREPARING PRADOFLOXACIN

The invention relates to an improved process for preparing pradofloxacin, in which the substituent in the 7 position is introduced by nucleophilic substitution in an N-methylpyrrolidone-ethanol solvent mixture.

Crystal modification B of 8-cyano-1-cyclopropyl-7-(1S,6S-2, 8-diazabicyclo[4.3.0]nonan-8-yl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

The present invention relates to a defined crystal modification of 8-cyano-1-cyclopropyl-7-(1S,6S-2,8-diazabicyclo[4.3.0]nonan-8-yl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid of the formula (I), to processes for its preparation and to its use in pharmaceutical preparations. The crystal modification can be distinguished from other crystal modifications of 8-cyano-1-cyclopropyl-7-(1S,6S-2,8-diazabicyclo[4.3.0]nonan-8-yl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid of the formula (I) by its characteristic X-ray powder diffractogram and its differential thermodiagram (see description).

Crystal modification C of 8-cyano-1-cyclopropyl-7-(1S,6S-2,8-diazabicyclo-[4.3.0]nonan-8-yl)-6-fluoro-1,4-dihyro-4-oxo-3-quinoline carboxylic

The present invention relates to a defined crystal modification of 8-cyano-1-cyclopropyl-7-(1S,6S-2,8-diazabicyclo[4.3.0]nonan-8-yl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid of the formula (1), to processes for its preparation and to its use in pharmaceutical preparations. The crystal modification can be distinguished from other crystal modifications of 8-cyano-1-cyclopropyl-7-(1S,6S-2,8-diazabicyclo[4.3.0]nonan-8-yl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid of the formula (1) by its characteristic X-ray powder diffractogram and its differential thermodiagram (see description).

Optionally substituted 8-cyano-1-cyclopropyl-7-(2,8-diazabicyclo[4.3.0]nonan-8-yl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids and their derivatives

Intermediates useful in the preparation of 8-cyano-1-cyclopropyl-7-(2,8-diazabicyclo[4.3.0]nonan-8-yl-6-fluorol,4-dihydro-4-oxo-3-quinolinecarboxylic acids of the following structures are claimed.