1. A process of preparing a fluoroquinolone enantiomer having Formula IV or salts thereof, the method comprising:
(a) contacting a first compound having Formula II with a third compound having Formula V to produce a fourth compound having Formula VI, wherein the fluoroquinolone having Formula IV, the first compound, the third compound, and the fourth compound are represented by
\u2003wherein R1 is selected from the group consisting of hydrogen, unsubstituted lower alkyl groups, substituted lower alkyl groups, cycloalkyl groups, unsubstituted C5-C24 aryl groups, substituted C5-C24 aryl groups, unsubstituted C5-C24 heteroaryl groups, substituted C5-C24 heteroaryl groups, and groups that can be hydrolyzed in living bodies; R3 is selected from the group consisting of hydrogen, unsubstituted lower alkyl groups, substituted lower alkyl groups, cycloalkyl groups, unsubstituted lower alkoxy groups, substituted lower alkoxy groups, unsubstituted C5-C24 aryl groups, substituted C5-C24 aryl groups, unsubstituted C5-C24 heteroaryl groups, substituted C5-C24 heteroaryl groups, unsubstituted C5-C24 aryloxy groups, substituted C5-C24 aryloxy groups, unsubstituted C5-C24 heteroaryloxy groups, substituted C5-C24 heteroaryloxy groups, and groups that can be hydrolyzed in living bodies; X is selected from the group consisting of halogen atoms; Y is CH2; Z is selected from the group consisting of oxygen and two hydrogen atoms; and R5 comprises a protected amino group having a formula or \u2014NR6, wherein R6 comprises a protecting group that is capable of leaving the protected amino group \u2014NR6; and
(b) contacting the fourth compound with a sufficient amount of a catalyst and at a condition sufficient to effect a cleavage of the protecting group R6 from the \u2014NR6 group, to produce a fluoroquinolone having Formula IV;
wherein the orientation of R2 is preserved throughout the process.
2. The process of claim 1, wherein R1 is selected from the group consisting of hydrogen, C1-C5 substituted and unsubstituted alkyl groups, C3-C10 cycloalkyl groups, C6-C14 substituted and unsubstituted aryl groups, C6-C14 substituted and unsubstituted heteroaryl groups, and groups that can be hydrolyzed in living bodies; R3 is selected from the group consisting of hydrogen, C1-C5 substituted and unsubstituted alkyl groups, C3-C10 cycloalkyl groups, C1-C5 substituted and unsubstituted alkoxy groups, C5-C14 substituted and unsubstituted aryl groups, C5-C14 substituted and unsubstituted heteroaryl groups, and C5-C14 substituted and unsubstituted aryloxy groups; R6 is selected from the group consisting of nitrophenylalkylidene, t-Boc, and Fmoc; and X is selected from the group consisting of Cl, F, and Br.
3. The process of claim 1, wherein R1 is selected from the group consisting of hydrogen, C1-C5 substituted and unsubstituted alkyl groups and groups that can be hydrolyzed in living bodies; R3 is selected from the group consisting of C3-C10 cycloalkyl groups; R6 comprises a nitrophenylalkylidene group; X is selected from the group consisting of Cl and F; Y comprises CH2; and Z comprises two hydrogen atoms.
4. The process of claim 1, wherein the catalyst is selected from the group consisting of acids and bases.
5. The process of claim 3, wherein the step of contacting is carried out at a temperature in a range from about room temperature to about 100\xb0 C.
6. The process of claim 3, wherein the catalyst is hydrochloric acid.
7. The process of claim 1, wherein the process further comprises recovering the enantiomer is carried out by recrystallization.
8. A process for preparing a fluoroquinolone carboxylic acid enantiomer having Formula Ia or salts thereof, the process comprising:
(a) contacting a compound having Formula IIa with a compound having Formula VIIa at a temperature in the range from about room temperature to about 100\xb0 C. for a time from about 10 minutes to about 7 days, to produce a compound having Formula VIa, wherein the fluoroquinolone having Formula Ia and the compounds having Formulae IIa, VIa, and VIIa are represent by
(b) contacting the compound having Formula VIa with an amount of HCl equal to about 0.1 to about 5 moles per mole of the compound having Formula VIIa at a temperature in the range from about room temperature to about 100\xb0 C., in a presence of methanol to produce the fluoroquinolone carboxylic acid having Formula Ia; and
(c) recovering the fluoroquinolone carboxylic acid enantiomer having Formula Ia;
wherein the orientation of the amino group is presented throughout the process.
9. The process of claim 8, wherein the step of recovering the fluoroquinolone carboxylic acid enantiomer is carried out by recrystallization.
The claims below are in addition to those above.
All refrences to claim(s) which appear below refer to the numbering after this setence.
1. A system for selectively controlling environmental conditions in an area of a surface of a dampening fluid layer disposed on an imaging member in a variable data lithographic image forming apparatus, comprising:
an enclosure disposed over a surface of a dampening fluid layer disposed on an imaging member, the enclosure substantially enclosing an area of the surface of the dampening fluid layer at which a radiation-based patterning subsystem selectively vaporizes portions of the dampening fluid layer; and
a gas-flow control subsystem coupled to the enclosure that controllably generates a gas flow within the enclosure and across the area of the surface of the dampening fluid layer at which the radiation-based patterning subsystem selectively vaporizes the portions of the dampening fluid layer, the gas-flow control subsystem including a humidity control subsystem that controls a humidity of a gas generated in the area of the surface of the dampening fluid layer at which the radiation-based patterning subsystem selectively vaporizes the portions of the dampening fluid layer,
the enclosure being configured (1) to permit an output of the radiation-based patterning subsystem to pass through the enclosure and to impinge on the area of the surface of the dampening fluid layer and (2) to permit the gas flow to exit the enclosure in a controlled manner at a desired location, and
the gas flow evacuating the gas including vaporized dampening fluid from the area of the surface of the dampening fluid layer.
2. The system of claim 1, the humidity control subsystem, comprising:
a pump having an inlet and an outlet, the outlet of the pump being communicatively connected to the enclosure; and
a desiccator material component disposed in a primary pathway for the gas flow between the outlet of the pump and the enclosure such that the gas flow from the outlet of the pump passes through the desiccator material component prior to being passed across the area of the surface of the dampening fluid layer in the enclosure.
3. The system of claim 2, the gas flow from the pump comprising air drawn from an ambient environment surrounding the variable data lithography image forming system through the inlet of the pump.
4. The system of claim 2, further comprising:
an alternate pathway for the gas flow from the outlet of the pump communicatively connecting the primary pathway and the enclosure; and
a bypass valve, disposed in the primary pathway that redirects at least a portion of the gas flow provided by the pump to the alternate pathway, to provide valve-operated humidity control for the gas flow through the enclosure and across the area of the surface of the dampening fluid layer.
5. The system of claim 1, further comprising an evacuation mechanism that is communicatively coupled to the enclosure for assisting with the evacuating the gas flow and the vaporized dampening fluid from the area of the surface of the dampening fluid layer.
6. The system of claim 5, further comprising a condensation mechanism for condensing the evacuated vaporized dampening fluid for recycling and reuse.
7. The system of claim 1, further comprising a wiper blade secured to the enclosure and disposed at a leading edge of the enclosure, relative to a direction of motion of the dampening fluid layer, the wiper blade governing a thickness of the dampening fluid layer, and limiting entry of at least one of air and contaminants into the enclosure and in the area of the surface of the dampening fluid layer.
8. The system of claim 1, the gas-flow control subsystem further comprising an air knife.
9. The system of claim 1, further comprising a local temperature control source that controls an environmental temperature within the enclosure and in the area of the surface of the dampening fluid layer.
10. The system of claim 9, the local temperature control source being located within the enclosure.
11. The system of claim 10, the local temperature control source being selected form a group consisting of: a heating coil, a heat lamp, a heated air source, and a cooled air source.
12. The system of claim 1, the gas-flow control subsystem further comprising a vacuum vapor removal subsystem communicatively coupled to the enclosure downstream in the gas flow direction from the area of the surface of the dampening fluid layer relative to motion of the dampening fluid layer.
13. The system of claim 12, air upstream from the area of the surface of the dampening fluid layer relative to motion of the dampening fluid layer being prevented from entering the gas flow, and air downstream from the area of the surface of the dampening fluid layer relative to motion of the dampening fluid layer being preferentially directed into the gas flow.
14. The system of claim 1, further comprising a window structure coupled to the enclosure, the window structure being disposed between the radiation-based patterning subsystem and the area of the surface of the dampening fluid layer at which the radiation-based patterning subsystem selectively vaporizes the portions of the dampening fluid layer, such that radiation emitted by the radiation-based patterning subsystem passes through the window structure prior to impinging on the dampening fluid layer, the window structure preventing contamination of optics associated with the radiation-based patterning subsystem by vaporized portions of the dampening fluid layer.
15. The system of claim 1, the gas-flow control subsystem further comprising:
an air knife subsystem disposed within the enclosure and downstream from the area of the surface of the dampening fluid layer at which the radiation-based patterning subsystem selectively vaporizes the portions of the dampening fluid layer, such that an air knife gas flow formed by the air knife subsystem is directed toward the area of the surface of the dampening fluid layer in a direction into relative motion of the dampening fluid layer; and
a vacuum vapor removal subsystem disposed within the enclosure and upstream and opposite from the air knife subsystem relative the area of the surface of the dampening fluid layer at which the radiation-based patterning subsystem selectively vaporizes the portions of the dampening fluid layer.
16. A system for selectively controlling environmental conditions in an area of a surface of a dampening fluid layer disposed on an imaging member in a variable data lithographic image forming apparatus, comprising:
an enclosure disposed over a surface of a dampening fluid layer disposed on an imaging member, the enclosure substantially enclosing an area of the surface of the dampening fluid layer at which a radiation-based patterning subsystem selectively vaporizes portions of the dampening fluid layer;
a gas-flow control subsystem coupled to the enclosure that controllably generates a gas flow within the enclosure and across the area of the surface of the dampening fluid layer at which the radiation-based patterning subsystem selectively vaporizes the portions of the dampening fluid layer, comprising:
a humidity control subsystem that controls a humidity of a gas forming the gas flow through the enclosure;
a temperature control subsystem that controls the temperature across the area of the surface of the dampening fluid layer;
an evacuation mechanism communicatively coupled to the enclosure that substantially evacuates the gas flow and vaporized dampening fluid from the area of the surface of the dampening fluid layer at which the radiation-based patterning subsystem selectively vaporizes the portions of the dampening fluid layer.
17. The system of claim 16, further comprising:
a wiper blade secured to the enclosure and disposed at a leading edge of the enclosure, relative to a direction of motion of the dampening fluid layer, the wiper blade governing a thickness of the dampening fluid layer, and limiting air entry into the enclosure and in the area of the surface of the dampening fluid layer; and
a window structure coupled to the enclosure, the window structure being disposed between the radiation-based patterning subsystem and the area of the surface of the dampening fluid layer at which the radiation-based patterning subsystem selectively vaporizes the portions of the dampening fluid layer, such that radiation emitted by the radiation-based patterning subsystem passes through the window structure prior impinging on the dampening fluid layer, the window structure substantially preventing contamination of optics associated with the radiation-based patterning subsystem by vaporized portions of the dampening fluid layer.
18. A variable data lithographic image forming system, comprising:
an imaging member having an arbitrarily reimageable surface;
a dampening fluid subsystem that applies a layer of dampening fluid to the arbitrarily reimageable surface;
a patterning subsystem that selectively removes portions of the dampening fluid layer to produce a latent image in the dampening fluid layer;
an environmental control subsystem, comprising:
an enclosure disposed over an area of the reimageable surface, the enclosure having a window structure disposed in the enclosure and the enclosure being configured to permit an output of the patterning subsystem to pass through the enclosure and to impinge on the area of the surface of the dampening fluid layer for the selective removal of portions of the dampening fluid layer to produce the latent image in the dampening fluid layer;
a gas-flow control subsystem coupled to the enclosure to controllably generate a gas flow within the enclosure and in the area of the surface of the dampening fluid layer at which the radiation-based patterning subsystem selectively vaporizes the portions of the dampening fluid layer to evacuate vaporized dampening fluid from the area of the surface of the dampening fluid layer; and
a humidity control subsystem that controls a humidity of a gas forming the gas flow through the enclosure; and
an inking subsystem for applying ink over the arbitrarily reimageable surface layer such that the ink selectively occupies regions of the reimageable surface layer where dampening fluid is removed by the patterning subsystem to produce an inked latent image; and
an image transfer subsystem for transferring the inked latent image to an image receiving media substrate.