From nalidixic acid to 1st generation

N

C

O

F

O

-

O

HN

N

CH

3

nalidixic acid

Norfloxacin *

1. introduce a fluor atom

(flumequin)

2. modify naphthyridone

in quinolone  (oxolinic acid)

3. introduce a piperazine

1978

* Belgian patent 863,429, 1978 to Kyorin

N

N

C

O

C

2

H

5

O

-

O

H

3

C

1

2

3

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