Kinoloni

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SINTEZA 4-KINOLONOVPROTIMIKROBNIH UČINKOVIN

H3C H3C

N

N

O

O

OH

NALIDIKSNA KISLINA

Cl

N

HN N CH3

KLOROKIN

H3C

CH3

nujen del za aktivnost, vezavo na kompleks DNA/giraza ter transport

kontrola aktivnosti, doda k afiniteti na G(+)

R5

afiniteta do giraze, celična permeabilnost

F N

R

O

N

COOH x8

N R1

optimalen H, blizu vezavnemu mestu na girazi

R protibakterijski spekter in farmakokinetika

antianaerobna aktivnost in farmakokinetika

vpliv na celokupno jakost delovanja

I.

O

OH

O

O

H3C

N

N

H3C

GENE UČINK N

N

OH

O

N

N

HN

H3C

II. GENERA (SUBSTITU OH

O

O

F

O

OH

F

O

N

N

N

HN

N

HN CH3

OH

O OH

O

F O

F O

predstavnik N

N N H3C

N

N

N

O

CH3

H3C

CH3

III.

GENER (SUBST O

CH3

O

O

F

O

F

OH N

N

N

N F

N H2N

NH

OH

CH3

F

IV. GENER (TUDI 2-PI O

F

O

O

F

N

OH

N

OH

N

N

Cl

H2N

O

CH3

H2N

predstavnik

SINTEZA NALIDIKSNE KISLINE 1-etil-7-metil-4-okso-1,4-dihidro[1,8]naftiridin-3-karboksilna kislina

ENOKSACIN

Enoxacin; AT-2266; CI-919; PD-107779; Comprecin; Flumark; Penetrex; Enoxor; Almitil Chemical Name: 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid. CAS(R) Reg. No.: 74011-58-8. Phase: Launched-1986. Source: Dainippon Pharmaceutical; Almirall Prodesfarma; Pfizer; SmithKline Beecham; Recordati; Pierre Fabre; Bellon. Activity / Mechanism: Antibacterial Drugs; Quinolones.

SINTEZA ENOKSACINA 1-Etil-6-fluoro-1,4-dihidro-4-oxo-7-(1-piperazinil)-1,8-naftiridin-3-karboksilna kislina

SINTEZA ENOKSACINA- nadaljevanje

CIPROFLOKSACIN

Ciprofloxacin hydrochloride; Bay-o-9867 monohydrate; Ciproxin; Eni; Cipro; Ciflox; Ciloxan; Ciprobay; Oftacilox; Ciproxan Chemical Name: 1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid hydrochloride hydrate. CAS(R) Reg. No.: 86393-32-0; 85721-33-1 (free base, anhydrous) Phase: Launched-1986. Source: Bayer; SPI Pharm.; ICN; Alcon. Activity / Mechanism: Antibacterial Ophthalmic Drugs; Antibacterial Drugs; Treatment of Cystic Fibrosis; Quinolones.

SINTEZA CIPROFLOKSACINA

1-ciklopropil-6-fluoro-1,4-dihidro-4-okso-7-(1-piperazinil)-3-kinolin karboksilna kislina

NORFLOKSACIN

Norfloxacin; AM-715; MK-0366; Lexinor; Baccidal; Barazan; Sebercim; Fulgram; Noroxin; Norflo Chemical Name: 1-Ethyl-6-fluoro-7-(1-piperazinyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid. CAS(R) Reg. No.: 70458-96-7; 68077-27-0 (monoHCl) Phase: Launched-1984. Source: Ist. Biol. Chemioter. ABC; Merck & Co.; Merck Sharp & Dohme; ISF; AstraZeneca; Roberts. Activity / Mechanism: A

SINTEZA NORFLOKSACINA 1-etil-6-fluoro-7-(1-piperazinil)-4-okso-1,4-dihidro-3-kinolin karboksilna kislina

PEFLOKSACIN

Pefloxacin; EU 5306; RB 1589; Peflacine Chemical Name: 6-Fluoro-7-(4-methylpiperazino)-1-ethyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid. CAS(R) Reg. No.: 70458-92-3. Phase: Launched-1985. Source: Bellon. Activity / Mechanism: Antibacterial Drugs; Quinolones.

SINTEZA PEFLOKSACINA 6-fluoro-7-(4-metilpiperazino)-1-etil-1,4-dihidro-4-oksokinolin-3-karboksilna kislina keto skupina !!

OFLOKSACIN

LEVOFLOKSACIN S-izomer

Ofloxacin; DL-8280; Hoe-280; Floxin; Ocuflox; Tarivid Chemical Name: (±)-9-Fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido [1,2,3-de]-1,4-benzoxazine-6-carboxylic acid. CAS(R) Reg. No.: 82419-36-1. Phase: Launched-1985. Source: Daiichi Pharmaceutical; Aventis Pharma; Allergan; Ortho-McNeil. Activity / Mechanism: Antibacterial Ophthalmic Drugs; Antibiotics; Antibacterial Drugs; Quinolones.

SINTEZA OFLOKSACINA (±)-9-fluoro-3-methyl-10-(4-metil-1-piperazinil)-7-okso-2,3-dihidro-7H-pirido [1,2,3-de]-1,4benzoksazin-6-karboksilna kislina

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