From nalidixic acid to 1st generation

N

N

C

O

C

2

H

5

O

-

O

H

3

C

N

C

O

F

O

-

O

HN

N

-

H

3

C

N

C

O

O

-

O

HN

N

N

C

O

O

-

O

N

N

CH

3

CH

3

F

F

nalidixic acid

norfloxacin

ciprofloxacin *

pefloxacin

cyclopropyl to

increase potency

* Ger. pat. 3,142,854 to Bayer AG, 1983

O

CH

3

-

H

3

C

N

C

O

O

-

O

N

N

F

ofloxacin

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