Skip to main content

The Chemistry of the Quinolones: Methods of Synthesizing the Quinolone Ring System

  • Chapter

Part of the book series: Handbook of Experimental Pharmacology ((HEP,volume 127))

Abstract

The quinolones, similar to the sulfonamides and nitrofurans, are totally synthetic chemical compounds used to combat infections (Albrecht 1977). They are derived by substitution of 1,4-dihydro-4-oxo-quinoline-3-carboxylic acids (structural formula 1) at the nitrogen atom of position 1.

This is a preview of subscription content, log in via an institution.

Buying options

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Abdalla GM, Sowell JW Sr (1987) Synthesis of 8-cyano-l,4-dihydro-4-oxopyrrolo[l,2- a]pyrimidine-3-carboxylic acids as potential antimicrobial agents. J Heterocycl Chem 24:297

    Article  CAS  Google Scholar 

  • Abdalla GM, Sowell JW (1990) Synthesis of 3-benzoyl-4,7-dihydro-7-oxopyrrolo[3,2- b]pyridine-6-carboxylic acid derivatives as potential antimicrobial agents. J Heterocycl Chem 27:1201

    Article  CAS  Google Scholar 

  • Abdulla RF, Emmrick TL, Taylor HM (1977a) A new synthetic approach to 4(lh)- pyridone derivatives. I. l-Alkyl-3,5-diaryl-4(lh)-pyridones. Synth Commun 7:305

    Article  CAS  Google Scholar 

  • Abdulla RF, Fuhr KH, Taylor HM (1977b) New synthetic approaches to 4(lh)- pyridones. II. Derivatives having nonaromatic substituents. Synth Commun 7:313

    Article  CAS  Google Scholar 

  • Agui H, Mitani T, Nakashita M, Nakagome T (1971) Studies on quinoline derivatives and related compounds. I. A new synthesis of l-alkyl-l,4-dihydro-4-oxo-3-quinolinecarboxylic acids. J Heterocycl Chem 8:357

    Article  CAS  Google Scholar 

  • Agui H, Komatsu T, Nakagome T (1975a) Studies on quinoline derivatives and related compounds. II. Synthesis of 5-substituted l-ethyl-l,4-dihydro-4-oxo-3-quinolinecarboxylic acid (1). J Heterocycl Chem 12:557

    Article  CAS  Google Scholar 

  • Agui H, Tobiki H, Nakagome T (1975b) Studies on quinoline derivatives and related compounds. III. A novel pyridine synthesis to give substituted l,4-dihydro-4-oxonicotinic acids (1). J Heterocycl Chem 12:1245

    Article  CAS  Google Scholar 

  • Albrecht R (1977) Development of antibacterial agents of the nalidixic acid type. Prog Drug Res 21:9

    PubMed  CAS  Google Scholar 

  • Altreuther P (1987) Data on chemistry and toxicology of Baytril. Vet Med Rev 2:87

    Google Scholar 

  • Ames DE, Chapman RF, Kucharska HZ (1964) Cinnolines. V.l. Methylation of some substituted cinnolines. J Chem Soc 5659

    Google Scholar 

  • Ames DE, Leung OT, Singh AG (1983) Synthesis of l-aryl-4-oxo-lH,4H-cinnoline-3- carboxylic acid esters. Synthesis 52

    Google Scholar 

  • Aoki M, Kamata M, Otsuka T, Shimma N, Yokose K (1988) European patent 259 804 (12.09.1986), Hoffmann-La Roche. Chem Abstr 109:73478r

    Google Scholar 

  • Atarashi S, Yokohama S, Yamazaki K, Sakano K, Imamura M, Hayakawa I (1987) Synthesis and antibacterial activities of optically active ofloxacin and its fluoromethyl derivative. Chem Pharm Bull (Tokyo) 35:1896

    Article  CAS  Google Scholar 

  • Atarashi S, Tsurumi H, Fujiwara T, Hayakawa I (1991) Asymmetric reduction of 7,8- difluoro-3-methyl-2H-l,4-benzoxazine. Synthesis of a key intermediate of (S)-(-)- Ofloxacin (DR-3355). J Heterocycl Chem 28:329

    Article  CAS  Google Scholar 

  • Atarashi S, Imamura M, Kimura Y, Yoshida A, Hayakawa I (1993) Fluorocyclopropyl quinolones. 1. Synthesis and structure-activity relationships of l-(2- fluorocyclopropyl)-3-pyridonecarboxylic acid antibacterial agents. J Med Chem 36:3444

    Article  PubMed  CAS  Google Scholar 

  • Augeri DJ, Fray AH, Kleinman EF (1990) Synthesis and antibacterial activity of 2,3- dehydroofloxacin. J Heterocycl Chem 27:1509

    Article  CAS  Google Scholar 

  • Bacon ER, Daum SJ (1991) Synthesis of 7-ethyl-4,7-dihydro-4-oxo-2-(4- pyridinyl)thieno[2,3-b]pyridine-5-carboxylic acid. J Heterocycl Chem 28:1953

    Article  CAS  Google Scholar 

  • Balogh M, Hermecz I, Meszaros Z, Simon K, Pusztay L, Horvath G, Dvortsak P (1980) Studies on chemotherapeutics. I. Synthesis of 5-substituted-4-oxo-l,4-dihydro-3-pyridinecarboxylic acid derivatives. J Heterocycl Chem 17:359

    Article  Google Scholar 

  • Barber HJ, Washbourn K, Wragg WR (1961) A new cinnoline synthesis. I. Cyclisation of mesoxalyl chloride phenylhydrazones to give substituted 4-hydroxycinnoline-3-carboxylic acids. J Chem Soc 2828

    Google Scholar 

  • Barker JM, Huddleston PR, Jones AW (1978) Thienyl analogues of the alkaloids. 3. Analogues of echinorine and echinopsine; a convenient synthesis of thieno [3,2-b] pyridines. J Chem Res 393

    Google Scholar 

  • Bassini C, Bismara C, Carlesso R, Feriano A, Gaviraghi G, Marchioro C, Perboni A, Shaw RE, Tamburini B, Tarzia G, Xerri L (1993) Synthesis and antimicrobial activity of DNA-gyrase inhibiting derivatives of 4-oxo-l,4-dihydro-3- pyridinecarboxylic acid. Farmaco [Sci] 48:159

    CAS  Google Scholar 

  • Bauditz R (1987) Results of clinical studies with Baytril in calves and pigs. Vet Med Rev 2:122

    Google Scholar 

  • Bayomi SM, Price KE, Sowell JW (1985) Synthesis of 7-oxopyrrolo[3,2-b] pyridine-6- carboxylic acid derivatives as potential antimicrobial agents. J Heterocycl Chem 22:83

    Article  CAS  Google Scholar 

  • Bell MR, Zalay AW, Oesterlin R, Schane P, Potts GO (1970) Basic ethers of l-(p- hydroxyphenyl)-2-phenyl-l,2,3,4-tetrahydroquinoline and l-(p-hydroxyphenyl)-2- phenylindole. Antifertility agents. J Med Chem 13:664

    Article  PubMed  CAS  Google Scholar 

  • Biere H, Seelen W (1976) Verfahren zur Darstellung von 4-oxo-l,4- dihydropyridincarbonsäurederivaten. Liebigs Ann Chem 1972

    Google Scholar 

  • Boamah PY, Haider N, Heinisch G (1990) Pyrido [2,3-c]pyridazines structurally related to nalidixic acid. Arch Pharm (Weinheim) 323:207

    Article  CAS  Google Scholar 

  • Borsche W, Herbert A (1941) Synthesen mit 5-Nitro-2-brom-acetophenon. Liebigs Ann Chem 546:293

    Article  CAS  Google Scholar 

  • Bouzard D, Di Cesare P, Essiz M, Jacquet JP, Remuzon P, Weber A, Oki T, Masuyoshi M (1989) Fluoronaphthyridines and quinolones as antibacterial agents. 1. Synthesis and structure-activity relationships of new 1-substituted derivatives. J Med Chem 32:537

    Article  PubMed  CAS  Google Scholar 

  • Bouzard D, Di Cesare P, Essiz M, Jacquet JP, Kiechel JR, Remuzon P, Weber A, Oki T, Masuyoshi M, Kessler RE, Fung-Tome J, Desiderio J (1990) Fluoronaphthyridines and quinolones as antibacterial agents. 2. Synthesis and structure-activity relationships of new 1-tert-butyl 7-substituted derivatives. J Med Chem 33:1344

    Article  PubMed  CAS  Google Scholar 

  • Bouzard D, Di Cesare P, Essiz M, Jacquet JP, Ledonssal B, Remuzon P, Kessler RE, Fung-Tome J (1992) Fluoronaphthyridines as antibacterial agents. 4. Synthesis and structure-activity relationships of 5-substituted-6-fluoro-7- (cycloalkylamino)-l,4-dihydro-4-oxo-l,8-naphthyridine-3-carboxylic acids. J Med Chem 35:518

    Article  PubMed  CAS  Google Scholar 

  • Braish TF, Fox DE (1990) Synthesis of (S,S)- and (R,R)-2-alkyl-2,5- diazabicyclo[2.2.1]heptanes. J Org Chem 55:1684

    Article  CAS  Google Scholar 

  • Bridges AJ, Sanchez JP (1990) Synthesis of 7-amino-l,4-dihydro-4-oxo-6- (trifluoromethyl)-l,8-naphthyridines. The use of methylidenemalonate as an activating group and a sulfur assisted cyclization. J Heterocycl Chem 27:1527

    Article  Google Scholar 

  • Brundage RP, Lesher GY (1976) US patent 3 928 366 (10.03.1974), Sterling Drug. Chem Abstr 84:74253

    Google Scholar 

  • Camps R (1901) Von der Amidophenylpropiolsäure zur Kynurensäure und deren Verwandten. Chem Ber 34:2703

    Article  CAS  Google Scholar 

  • Cecchetti V, Fravolini A, Fringuelli R, Mascellani G, Pagella PG, Palmioli M, Segre G, Terni P (1987) Synthesis of 7,12-dihydropyrido[3,4-b:5,4-b]diindoles. A novel class of rigid, planar benzodiazepine receptor ligands. J Med Chem 30:456

    Article  Google Scholar 

  • Cecchetti V, Fravolini A, Schiafella F (1991) One-pot synthesis of rufloxacin. Synth Commun 21:2301

    Article  CAS  Google Scholar 

  • Cecchetti V, Fravolini A, Pagella PG, Savino A, Tabarrini O (1993) Quinoline- carboxylic acids. 3. Synthesis and antibacterial evaluation of 2-substituted-7-oxo- 2,3-dihydro-7H-pyrido[l,2,3-de] [l,4]benzothiazine-6-carboxylic acids related to rufloxacin. J Med Chem 36:3449

    Article  PubMed  CAS  Google Scholar 

  • Chiarino D, Napoletano M, Sala A (1988) Synthesis of 4,7-dihydro-4-oxoisoxazolo[5,4- b]pyridine-5-carboxylic acid derivatives as potential antimicrobial agents. J Heterocycl Chem 25:231

    Article  CAS  Google Scholar 

  • Chu DTW (1985a) South African patent 852 802 (27.11.1985), Abbott Lab. Chem Abstr 106:213930x

    Google Scholar 

  • Chu DTW (1985b) A regiospecific synthesis of l-methylamino-6-fluoro-7-(4- methylpiperazin-l-yl)-l,4-dihydro-4-oxoquinoline-3-carboxylic acid. J Heterocycl Chem 22:1033

    Article  CAS  Google Scholar 

  • Chu DTW (1990) Syntheses of 6-fluoro-7-piperazin-l-yl-9-cyclopropyl-2,3,4,9- tetrahydroisothiazolo[5,4-b]quinoline-3,4-dione and 6-fluoro-7-piperazin-l-yl-9- p-fluorophenyl-2,3,4,9-tetrahydroisothiazolo[5,4-b] quinoline-3,4-dione. J Heterocycl Chem 27:839

    Article  CAS  Google Scholar 

  • Chu DTW, Claiborne AK (1987) Short syntheses of l,2,3,5-tetrahydrp-5- oxopyrrolo[l,2-a]quinoline-4-carboxylic acid and l,2,3,4-tetrahydro-6H-6- oxopyrido[l,2-a]quinoline-5-carboxylic acid derivatives. J Heterocycl Chem 24:1537

    Article  CAS  Google Scholar 

  • Chu DTW, Claiborne AK (1990) Practical synthesis of iminochlorothioformates: application of iminochlorothioformates in the synthesis of novel 2,3,4,9- tetrahydroisothiazolo[5,4b][l,8]naphthyridine-3,4-diones and 2,3,4,9-tetrahy- droisothiazolo[5,4-b]quinoline-3,4-dione derivatives. J Heterocycl Chem 27: 1191

    Article  CAS  Google Scholar 

  • Chu DTW, Fernandes PB, Claiborne AK, Pihuleac E, Nordeen CW, Maleczka RE Jr, Pernet AG (1985) Synthesis and structure-activity relationships of novel arylfluoroquinolone antibacterial agents. J Med Chem 28:1558

    Article  PubMed  CAS  Google Scholar 

  • Chu DTW, Fernandes PB, Pernet AG (1986) Synthesis and biological activity of benzothiazolo [3,2-a] quinolone antibacterial agents. J Med Chem 29:1531

    Article  PubMed  CAS  Google Scholar 

  • Chu DTW, Lee CM, Li Q, Cooper CS, Plattner JJ (1992) WO 9 116 894 (02.05.1990), Abbott Lab. Chem Abstr 117:26583b

    Google Scholar 

  • Coburn RA, Gala D (1982) Synthesis of 8-amino-6-methoxycinnoline. A precursor for 2-azaprimaquine. J Heterocycl Chem 19:757

    Article  CAS  Google Scholar 

  • Culbertson TP (1991) Synthesis of 4H-l,4-benzothiazine 1-oxide and 1,1-dioxide. Analogs of quinolone antibacterial agents. J Heterocycl Chem 28:1701

    Article  CAS  Google Scholar 

  • Dalhoff A, Petersen U, Endermann R (1996) In vitro activity of BAY 12–8039, a new methoxyquinolone. Chemotherapy (Basel) 42:410–425

    CAS  Google Scholar 

  • Di Cesare P, Bouzard D, Essiz M, Jacquet JP, Ledonssal B, Kiechel JR, Remuzon P, Kessler RE, Fung-Tome J, Desiderio J (1992) Fluoronaphthyridines and quinolones as antibacterial agents. 5. Synthesis and antimicrobial activity of chiral l-tert-butyl-6-fluoro-7-substituted-naphthyridones. J Med Chem 35:4205

    Article  PubMed  Google Scholar 

  • Dohmori R, Kadoya S, Takamura I, Suzuki N (1976) Synthetic chemotherapeutic agents. I. Synthesis of 2-substituted thiazolo [5,4-f] quinoline derivatives. Chem Pharm Bull (Tokyo) 24:130

    Article  CAS  Google Scholar 

  • Domagala JM, Heifetz CL, Hutt MP, Mich TF, Nichols JB, Solomon M, Worth DF (1988) 1-substituted 7-[3-[(ethylamino)methyl]-l-pyrrolidinyl]-6,8-difluoro-l,4- dihydro-4-oxo-3-quinolinecarboxylic acids. New quantitative structure-activity relationships at N2 for the quinolone antibacterials. J Med Chem 31:991

    Article  PubMed  CAS  Google Scholar 

  • Dowlatshahi HA (1985) Synthesis of ethyl 7-methoxy-4-oxocinnoline-3-carboxylate. Synth Commun 15:1095

    Article  CAS  Google Scholar 

  • Egawa H, Miyamoto T, Minamida A, Nishimura Y, Okada H, Uno H, Matsumoto J (1984) Pyridonecarboxylic acids as antibacterial agents. 4. Synthesis and antibacterial activity of 7-(3-amino-l-pyrrolidinyl)-l-ethyl-6-fluoro-l,4-dihydro-4-oxo-l,8- naphthyridine-3-carboxylic acid and its analogues. J Med Chem 27:1543

    Article  PubMed  CAS  Google Scholar 

  • Egawa H, Miyamoto T, Matsumoto J (1986) A new synthesis of 7H-pyrido[l,2,3- de][l,4]benzoxazine derivatives including an antibacterial agent, ofloxacin. Chem Pharm Bull (Tokyo) 34:4038

    Article  Google Scholar 

  • Fengler G, Grohe K (1984) DOS 3 229 126 (04.08.1982) Bayer AG. Chem Abstr 100:209385g

    Google Scholar 

  • Fengler G, Arlt D, Grohe K (1984a) DOS 3 229 124 (04.08.1982) Bayer AG. Chem Abstr 101:90953u

    Google Scholar 

  • Fengler G, Arlt D, Grohe K, Zeiler H-J, Metzger K (1984b) DOS 3 229 125 (04.02.1982) Bayer AG, Chem Abstr 101:7176z

    Google Scholar 

  • Frigola J, Colombo A, Más J, Parés J (1987) Synthesis, structure elucidation and chemotherapeutic activity of 6-substituted l-ethyl-l,4-dihydro-7-[(l- imidazoly)phenyhnethyl]-4-oxo-3-quinolinecarboxylic acids. J Heterocycl Chem 24:399

    Google Scholar 

  • Fromtling RA, Castañer J (1996) Trovafloxacin-Mesylate. Drugs Fut 21:496–505

    Google Scholar 

  • Georgopapadakou NH, Dix BA, Angehrn P, Wick A, Olson GL (1987) Monocyclic and tricyclic analogs of quinolones: mechanism of action. Antimicrob Agents Chemother 31:614

    PubMed  CAS  Google Scholar 

  • Gerster JF (1973) DOS 2 264 163 (12.07.1973) Riker Laboratories Inc. Chem Abstr 79:92029y

    Google Scholar 

  • Goueffon Y, Montay G, Roquet F, Pesson M (1981) New synthetic antimicrobial agent: l,4-di-hydro-l-ethyl-6-fluoro-7-(4-methyl-l-piperazinyl)-4-oxo-quinoline-3-car- boxylic acid (1589 RB). C R Acad Sci Biol (Paris) 292:37

    CAS  Google Scholar 

  • Gould RG, Jacobs WA (1939) The synthesis of certain substituted quinolines and 5,6- benzoquinolines. J Am Chem Soc 61:2890

    Article  CAS  Google Scholar 

  • Grohe K (1986) DOS 3 502 935 (29.09.1984) Bayer AG. Chem Abstr 105:226051r

    Google Scholar 

  • Grohe K (1992) DOS 4 015 299 (14.11.1991) Bayer AG. Chem Abstr 117:4811y

    Google Scholar 

  • Grohe K (1993) The importance of the cycloaracylation process for the synthesis of modern fluoroquinolones. J Prakt Chem 335:397

    Article  CAS  Google Scholar 

  • Grohe K, Heitzer H (1987a) Synthese von 4-Chinolon-3-carbonsäuren. Liebigs Ann Chem 29

    Google Scholar 

  • Grohe K, Heitzer H (1987b) Synthese von l-Amino-4-chinolon-3-carbonsäuren. Liebigs Ann Chem 871

    Google Scholar 

  • Grohe K, Schriewer M (1987) DOS 3 522 406 (22.06.1985) Bayer AG. Chem Abstr 107:23351g

    Google Scholar 

  • Grohe K, Zeiler H-J, Metzger K (1980) DOS 2 808 070 (24.02.1978) Bayer AG. Chem Abstr 92:41916w

    Google Scholar 

  • Grohe K, Zeiler H-J, Metzger K (1981) DOS 2 903 850 (01.02.1979) Bayer AG. Chem Abstr 95:43152e

    Google Scholar 

  • Grohe K, Zeiler H-J, Metzger K (1983) DOS 3 142 854 (29.10.1981) Bayer AG. Chem Abstr 99:53790h

    Google Scholar 

  • Grohe K, Petersen U, Zeiler H-J, Metzger K (1985) DOS 3 318 145 (18.05.1983) Bayer AG. Chem Abstr 102:78744q

    Google Scholar 

  • Grohe K, Zeiler H-J, Metzger K (1986) DOS 3 409 922 (17.03.1984) Bayer AG. Chem Abstr 104:88589y

    Google Scholar 

  • Hägen SE, Domagala JM, Heifetz CL, Johnson J (1991) Synthesis and biological activity of 5-alkyl-l,7,8-trisubstituted-6-fluoroquinoline-3-carboxylic acids. J Med Chem 34:1155

    Article  PubMed  Google Scholar 

  • Harris ND (1991) Cyclization of diethyl 3,4-diisobutoxyanilino-methylenemalonate. Synthesis 256

    Google Scholar 

  • Hayakawa I, Kimura Y (1990) European patent 341 493 (27.04.1988), Daiichi Seiyaku. Chem Abstr 113:40473f

    Google Scholar 

  • Hayakawa I, Tanaka Y (1984) Facile synthesis of thiazolo[4,5-b]- and thieno[3,2- b]pyridine derivatives by a novel pyridine cyclization reaction via enamine intermediates. Heterocycles 22:1697

    Article  CAS  Google Scholar 

  • Hayakawa I, Hiramitsu T, Tanaka Y (1984) Synthesis and antibacterial activities of substituted 7-oxo-2,3-dihydro-7H-pyrido[l,2,3-de] [1,4]benzoxazine-6-carboxylic acids. Chem Pharm Bull (Tokyo) 32:4907

    Article  CAS  Google Scholar 

  • Hayakawa I, Atarashi S, Yokohama S, Imamura M, Sakano M, Furukawa M (1986) Synthesis and antibacterial activities of optically active ofloxacin. Antimicrob Agents Chemother 29:163

    PubMed  CAS  Google Scholar 

  • Heindl J, Keim HW, Dogs E, Seeger A, Herrmann C (1977) Untersuchungen über die antibakterielle Aktivität von Chinoloncarbonsäuren. IX (1). Azaanaloga. Di- und trisubstituierte l,4-Dihydro-4-oxo-l,5-naphthyridin-3-carbonsäuren und 1-Äthyl- 4-pyridon-3-carbonsäure. Eur J Med Chem 12:549

    CAS  Google Scholar 

  • Hirose T, Mishio S, Matsumoto J, Minami S (1982) Pyridone-carboxylic acids as antibacterial agents. I. Synthesis and antibacterial activity of l-alkyl-l,4-dihydro-4- oxo-1,8- and l,6-naphthyridine-3-carboxylic acids. Chem Pharm Bull (Tokyo) 30:2399

    Article  CAS  Google Scholar 

  • Högberg T, Khannal I, Drake SD, Mitscher LA, Shen LL (1984) Structure-activity relationships among DNA gyrase inhibitors. Synthesis and biological evaluation of 1,2-dihydro-4,4-dimethyl-1-oxo-2-naphthalenecarboxylic acids as 1-carba bioisosteres of oxolinic acid. J Med Chem 27:306

    Article  PubMed  Google Scholar 

  • Huffman KR, Schaefer FC, Peters GA (1962) Reaction of s-triazine with acidic a-methylene compounds. J Org Chem 27:551

    Article  CAS  Google Scholar 

  • Irikura T, Koga H, Murayama S (1981) Belgian patent 887 574 (19.08.1980), Kyorin Pharm Co. Chem Abstr 95:187096n

    Google Scholar 

  • Irikura T, Suzue S, Murayama S, Hirai K, Ishizaki T (1987) European patent 195 316 (08.03.1985), Kyorin Pharm. Chem Abstr 106:50068f

    Google Scholar 

  • Ishikawa H, Tabusa F, Miyamoto H, Kano M, Ueda H, Tamaoka H, Nakagawa K (1989)Studies on antibacterial agents. I. Synthesis of substituted 6,7-dihydro-l- oxo-lH,5H-benzo[i,j]-quinolizine-2-carboxylic acids. Chem Pharm Bull (Tokyo) 37:2103

    Article  CAS  Google Scholar 

  • Ishikawa H, Uno T, Miyamoto H, Ueda H, Tamaoka H, Tominage M, Nakagawa K (1990)Studies on antibacterial agents. II. Synthesis and antibacterial activities of substituted l,2-dihydro-6-oxo-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acids. Chem Pharm Bull (Tokyo) 38:2459

    Article  CAS  Google Scholar 

  • Ishizaki T, Suzue S, Irikura T (1985) New synthesis of fluoroquinolonecarboxylic acid. J Chem Soc Jpn 10:2054

    Google Scholar 

  • Itoh Y, Kato H, Ogawa N, Koshinaka E, Suzuki T, Yagi N (1985) DOS 3 433 924 (19.09.1983), Horikuri Pharm Co. Chem Abstr 103:123517b

    Google Scholar 

  • Jefson MR, McGuirk (1988) European patent 215 650 (18.05.1985), Pfizer Inc. Chem Abstr 108:94417q

    Google Scholar 

  • Jefson MR, McGuirk PR (1989) US patent 4 775 668 (19.08.1986), Pfizer Inc. Chem Abstr 110:57534w

    Google Scholar 

  • Jinbo Y, Kondo H, Inoue Y, Taguchi M, Tsujishita H, Kotera Y, Sakamoto F, Tsukamoto G (1993a) J Med Chem 36:2621

    Article  PubMed  CAS  Google Scholar 

  • Itoh Y, Kato H, Ogawa N, Koshinaka E, Suzuki T, Yagi N (1985) DOS 3 433 924 (19.09.1983), Hokuriku Pharm Co. Chem Abstr 103:123517b

    Google Scholar 

  • Jefson MR, McGuirk PR (1988) European patent 215 650 (18.05.1985), Pfizer Inc. Chem Abstr 108:94417q

    Google Scholar 

  • Jefson MR, McGuirk PR (1989) US patent 4 775 668 (19.08.1986), Pfizer Inc. Chem Abstr 110:57534w

    Google Scholar 

  • Jinbo Y, Kondo H, Inoue Y, Taguchi M, Tsujishita H, Kotera Y, Sakamoto F, Tsukamoto G (1993a) Synthesis and antibacterial activity of a new series of tetracyclic pyridone carboxylic acids. J Med Chem 36:2621

    Article  PubMed  CAS  Google Scholar 

  • Jinbo Y, Taguchi M, Inoue Y, Kondo H, Miyasake T, Tsujishida H, Sakamoto F, Tsukamoto G (1993b) Synthesis and antibacterial activity of a new series of tetracyclic pyridone carboxylic acids. J Med Chem 36:3148

    Article  PubMed  CAS  Google Scholar 

  • Jinbo Y, Kondo H, Inoue Y, Taguchi M, Tsujishita H, Kotera Y, Sakamoto F, Tsukamoto G (1994) Synthesis and antibacterial activity of thiazolopyrazine- incorporated tetracyclic quinolone antibacterials. J Med Chem 37:586

    Article  PubMed  Google Scholar 

  • Jordis U, Sauter F, Rudolf M, Gan C (1988) Synthesen neuer Chinolon- Chemotherapeutika, 1. Mitt. Pyridochinoline und Pyridophenanthroline als “lin- benzo-Nalidixinsäure”-Derivate. Monatsschr Chem 119:761

    Article  CAS  Google Scholar 

  • Kametani T, Kigasawa K, Hiiragi M, Wakisaka K, Kusama O, Sugi H, Kawasaki K (1977) Synthetic studies on chemotherapeutics. II. (1) Synthesis of phenyl- substituted l,4-dihydro-4-oxonicotinic acid derivatives. [Studies on the syntheses of heterocyclic compounds. Part 704 (2)]. J Heterocycl Chem 14:477

    Article  CAS  Google Scholar 

  • Kaminsky D, Meltzer RJ (1968) Quinolone antibacterial agents. Oxolinic acid and related compounds. J Med Chem 11:160

    Article  PubMed  CAS  Google Scholar 

  • Kilbourn EE, Seidel MS (1972) Synthesis of n-alkyl-3-carboxy-4-pyridones. J Org Chem 37:1145

    Article  CAS  Google Scholar 

  • Kimura Y, Miyamoto T, Matsumoto T, Minami S (1976) Syntheses of pyrimido[4,5- c]pyridazine derivatives. I. A novel reaction of a-diazo-j3-oxo-5-(4-chloropyri- midine)propionate with hydrazine leading to l,2-dihydro-4-hydroxypyrimido[4,5- c]pyridazine-3-carboxamide. Chem Pharm Bull (Tokyo) 24:2637

    Article  CAS  Google Scholar 

  • Koga H, Itoh A, Murayama S, Suzue S, Irikura T (1980) Structure-activity relationships of antibacterial 6,7- and 7,8-disubstituted l-alkyl-l,4-dihydro-4- oxoquinoline-3-carboxylic acids. J Med Chem 23:1358

    Article  PubMed  CAS  Google Scholar 

  • Kondo H, Taguchi M, Inoue Y, Sakamoto F, Tsukamoto G (1990) Synthesis and antibacterial activity of thiazolo-, oxazolo-, and imidazolo[3,2-a][l,8]naphthyri- dinecarboxylic acids. J Med Chem 33:2012

    Article  PubMed  CAS  Google Scholar 

  • Laborde E, Kiely JS, Culbertson TP, Lesheski LE (1993) Quinolone antibacterials: synthesis and biological activity of carbon isosteres of the 1-piperazinyl and 3- amino-l-pyrrolidinyl side chains. J Med Chem 36:1964

    Article  PubMed  CAS  Google Scholar 

  • Le Hao Dong P, Coquelet C, Bastide JM, Lebecq JC (1981) Nouveaux agents antibactériens II. Dérivés pyrazolo-azaquinoléiniques. Eur J Med Chem Chim Ther 16:39

    Google Scholar 

  • Lesher GY, Carabateas PM (1973) DOS 2 224 090 (30.11.1972), Sterling Drug Inc. Chem Abstr 78:84280n

    Google Scholar 

  • Lesher GY, Froelich EJ, Gruett MD, Bailey JH, Brundage RP (1962) 1,8- naphthyridine derivatives. A new class of chemotherapeutic agents. J Med Pharm Chem 5:1063

    Article  CAS  Google Scholar 

  • Leysen DC, Haemers A, Bollaert W (1984) Thiazolopyridine analogs of nalidixic acid. 2. Thiazolo[4,5-b]pyridines. J Heterocycl Chem 21:1361

    Article  CAS  Google Scholar 

  • Liu J, Guo H (1992) Synthesis and antibacterial activity of 1-(substituted pyrrolyl)- 7-(substituted amino)-6-fluoro-l,4-dihydro-4-oxo-3-quinolinecarboxylic acids. J Med Chem 35:3469

    Article  PubMed  CAS  Google Scholar 

  • Markees DG, Schwab LS, Vegotsky A (1974) Synthesis and antibacterial activity of some substituted 4-quinolone-3-carboxylic acids. J Med Chem 17:137

    Article  PubMed  CAS  Google Scholar 

  • Matsumoto J, Minami S (1975) Pyrido [2,3-d] pyrimidine antibacterial agents. 3.8-alkyl- and 8-vinyl-5,8-dihydro-5-oxo-2-(l-piperazinyl)pyrido[2,3-d]pyrimidine-6-car- boxylic acids and their derivatives. J Med Chem 18:74

    Article  PubMed  CAS  Google Scholar 

  • Matsumoto J, Miyamoto T, Minamida A, Nishimura Y, Egawa H, Nishimura H (1984a) Synthesis of fluorinated pyridines by the Balz-Schiemann Reaction. An alternative route to enoxacin, a new antibacterial pyridonecarboxylic acid. J Heterocycl Chem 21:673

    Article  CAS  Google Scholar 

  • Matsumoto J, Miyamoto T, Minamida A, Nishimura Y, Egawa H, Nishimura H (1984b) Pyridonecarboxylic acids as antibacterial agents. 2. Synthesis and structure-activity relationships of 1,6,7-trisubstituted 1,4-dihydro-4-oxo-l,8- naphthyridine-3-carboxylic acids, including enoxacin, a new antibacterial agent. J Heterocycl Chem 27:292

    CAS  Google Scholar 

  • Matsumoto J, Miyamoto T, Egawa H, Nakamura S (1988) European patent 242 789 (25.04.1986), Dainippon Pharm. Chem Abstr 108:150325x

    Google Scholar 

  • Meth-Cohn O (1986) The synthesis of quinolines from N-alkylformanilides and activated acetic acids. Synthesis 76

    Google Scholar 

  • Minami S, Shono T, Matsumoto J (1971) Pyrido [2,3-d] pyrimidine antibacterial agents. II. Piromidic acid and related compounds. Chem Pharm Bull (Tokyo) 19:1426

    Article  CAS  Google Scholar 

  • Mitscher LA, Flynn DL, Gracey HE, Drake SD (1979) Quinolone antimicrobial agents. 2. Methylenedioxy positional isomers of oxolinic acid. J Med Chem 22:1354

    Article  PubMed  CAS  Google Scholar 

  • Mitscher LA, Sharma PN, Chu DTW, Shen LL, Pernet AG (1987) Chiral DNA Gyrase inhibitors. 2. Asymmetric synthesis and biological activity of the enantiomers of 9- fluoro-3-methyl-10-(4-methyl-l-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[l,2,3- de]-l,4-benzoxazine-6-carboxylic acid (ofloxacin). J Med Chem 30:2283

    Article  PubMed  CAS  Google Scholar 

  • Miyamoto H, Ueda H, Otsuka T, Aki S, Tamaoka H, Tominaga M, Nakagawa K (1990) Studies on antibacterial agents. III. Synthesis and antibacterial activities of substituted l,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylic acids. Chem Pharm Bull (Tokyo) 38:2472

    Article  CAS  Google Scholar 

  • Miyamoto T, Matsumoto T (1988) A new cinnoline ring construction by the reaction of 2-diazo-3-(2-fluorophenyl)-3-oxopropionates with tri-n-butylphosphine. Chem Pharm Bull (Tokyo) 36:1321

    Article  CAS  Google Scholar 

  • Miyamoto T, Matsumoto J (1990a) Fluorinated pyrido[2,3-c]pyridazines. II. Synthesis and antibacterial activity of 1,7-disubstituted 6-fluoro-4-(lH)-oxopyrido[2,3- c]pyridazine-3-carboxylic acids. Chem Pharm Bull (Tokyo) 38:3359

    Article  CAS  Google Scholar 

  • Miyamoto T, Matsumoto T (1990b) Fluorinated pyrido[2,3-c]pyridazines. I. Reductive cyclization of ethyl 2-diazo-2-(5-fluoro-2-halonicotinoyl)acetate with trialkylphos- phine. Chem Pharm Bull (Tokyo) 38:3211

    Article  CAS  Google Scholar 

  • Miyamoto T, Egawa H, Matsumoto J (1987a) Pyridonecarboxylic acids as antibacterial agents. VIII. An alternative synthesis of enoxacin via fluoronicotinic acid derivatives. Chem Pharm Bull (Tokyo) 35:2280

    Article  CAS  Google Scholar 

  • Miyamoto T, Egawa H, Shibamori K, Matsumoto J (1987b) Synthesis and reactions of 7-substituted l-cyclopropyl-6-fluoro-l,4-dihydro-4-oxo-l,8-naphthyridine-3- carboxylic acids as an antibacterial agent. J Heterocycl Chem 24:1333

    Article  CAS  Google Scholar 

  • Miyamoto T, Matsumoto J, Chiba K, Egawa H, Shibamori K, Minamida A, Nishimura Y, Okada H, Kataoka M, Fujita M, Hirose T, Nakano J (1990) Synthesis and structure-activity relationships of 5-substituted 6,8-difluoroquinolones, including Sparfloxacin, a new quinolone antibacterial agent with improved potency. J Med Chem 33:1645

    Article  PubMed  CAS  Google Scholar 

  • Miyamoto T, Kimura Y, Matsumoto J, Minami S (1978) Syntheses of pyrimido[4,5- c]pyridazine derivatives. II. A novel reaction of a-diazo-j8-oxo-5-(4-chloropyrimi- dine)propionate with triphenyl phosphine leading to l,4-dihydro-4-oxopyrimido- [4,5-c] pyridazine-3-carboxylate. Chem Pharm Bull (Tokyo) 26:14

    Article  CAS  Google Scholar 

  • Moran DB, Ziegler CB Jr, Dunne TS, Kuck NA, Lin Y (1989) Synthesis of novel 5- fluoro analogues of norfloxacin and ciprofloxacin. J Med Chem 32:1313

    Article  PubMed  CAS  Google Scholar 

  • Nagano H, Yokota T, Katok Y (1990) European patent 342 675 (19.05.1988), Chugai Pharm. Chem Abstr 113:6175j

    Google Scholar 

  • Narita H, Konishi Y, Nitta J, Nagaki H, Kitayama I, Watanabe Y, Saikawa I (1986a) Pyridonecarboxylic acids as antibacterial agents. I. Synthesis and structure-activity relationship of l-aryl-6-(4-dimethylaminophenyl)-4-pyridone-3-carboxylic acids. Yakugaku Zasshi 106:775

    PubMed  CAS  Google Scholar 

  • Narita H, Konishi Y, Nitta J, Kobayashi Y, Watanabe Y, Minami S, Saikawa I (1986b) Pyridonecarboxylic acids as antibacterial agents. II. Synthesis and structure- activity relationship of l-(4-hydroxyphenyl)-6-substituted-4-pyridone-3- carboxylic acids. Yakugaku Zasshi 106:782

    PubMed  CAS  Google Scholar 

  • Narita H, Konishi Y, Nitta J, Miyazima M, Watanabe Y, Yotsuji A, Saikawa I (1986c) Pyridonecarboxylic acids as antibacterial agents. III. Synthesis and structure-activity relationship of l-(4-fluorophenyl)- and l-(2,4-difluorophenyl)-6-substituted-4- pyridone-3-carboxylic acids. Yakugaku Zasshi 106:788

    PubMed  CAS  Google Scholar 

  • Narita H, Konishi Y, Nitta J, Kittayama I, Miyazima M, Watanabe Y, Yotsuji A (1986d) Pyridonecarboxylic acids as antibacterial agents. V. Synthesis and structure-activity relationship of 7-amino-6-fluoro-l-(fluorophenyl)-4-oxo-l,8- naphthyridine-3-carboxylic acids. Yakugaku Zasshi 106:802

    PubMed  CAS  Google Scholar 

  • Narita H, Todo J, Nitta J, Nakagi H, Lino F, Miyajima M, Fukuoka Y, Saikawa I (1990) DOS 3 913 245 (23.04.1988), Toyama Chem. Chem Abstr 113:78417n

    Google Scholar 

  • Nishimura Y, Matsumoto J (1987) Pyridonecarboxylic acids as antibacterial agents. 9. Synthesis and antibacterial activity of 1-substituted 6-fluoro-l,4,-dihydro-4-oxo-7- (4-pyridyl)-l,8-naphthyridine-3-carboxylic acids. J Med Chem 30:1622

    Article  PubMed  CAS  Google Scholar 

  • O’Neill BT (1990) European patent 370 686 (23.11.1988), Pfizer Inc. Chem Abstr 113:191182v

    Google Scholar 

  • Ockenden DW, Schofield K (1953) Cinnolines. Part XXXIII. Some 3-aryl-4- hydroxycinnolines. J Chem Soc 3706

    Google Scholar 

  • Okada T, Tsuji T, Tsushima T, Ezumi K, Yoshida T, Matsuura S (1991a) Synthesis and antibacterial activities of novel oxazine and thiazine ring-fused tricyclic quinolonecarboxylic acids: 10-(alicyclic amino)-9-fluoro-7-oxo-7H-pyrido[l,2,3- de][l,4]benzoxazine-6-carboxylic acids and the corresponding 1-Thia congeners. J Heterocycl Chem 28:1067

    Article  CAS  Google Scholar 

  • Okada T, Tsuji T, Tsushima T, Yoshida T, Matsuura S (1991b) Synthesis and antibacterial activities of novel dihydrooxazine and dihydrothiazine ring-fused tricyclic quinolonecarboxylic acids: 9-fluoro-3-methylene-10-(4-methylpiperazin-l-yl)-7- oxo-2,3-dihydro-7H-pyrido[l,2,3-de][l,4]benzoxazine-6-carboxylic acid and its 1- Thia congeners. J Heterocycl Chem 28:1061

    Article  CAS  Google Scholar 

  • Okumura K, Inoue K, Tomie M, Adachi T, Kondo K (1974a) Japanese patent 7 410 519 (19.02.1969), Tanabe Seiyaku. Chem Abstr 81:120503k

    Google Scholar 

  • Okumura K, Inoue K, Tomie M, Adachi T, Kondo K (1974b) Japanese patent 7 410 520 (19.02.1969), Tanabe Seiyaku. Chem Abstr 81:120504m

    Google Scholar 

  • Otsubo J, Manabe Y, Kazuyuki K (1982) Belgian patent 891 537 (18.12.1980), Otsuka Pharm Co. Chem Abstr 97:92321j

    Google Scholar 

  • Parikh VD, Fray AH, Kleinman EF (1988) Synthesis of 8,9-difluoro-2-methyl-6-oxo- l,2-dihydropyrrolo[3,2,1-ij]quinoline-5-carboxylic acid. J Heterocycl Chem 25:1567

    Article  CAS  Google Scholar 

  • Pesson M, Chabassier S (1974) Chimie organique — nitriles et amide-oximes d’acides alkyl-8 oxo-5 dihydro-5.8 pyrido [2,3-d] pyrimidine-6 carboxyliques. C R Acad Sci [C] 279:413

    CAS  Google Scholar 

  • Pesson M, Antoine M, Chabassier S, Geiger S, Girard P, Richer D, de Lajudie P, Horvath E, Leriche B, Patte S (1974a) Antibactériens dérivés des acides alkyl-8- oxo-5-dihydro-5,8 pyrido [2,3-d] pyrimidine-6 carboxyliques. I. Nouveau procédé de préparation. Eur J Med Chem Chim Ther 9:585

    CAS  Google Scholar 

  • Pesson M, Antoine M, Chabassier S, Girard MP, Richer D (1974b) Chimie organique. Synthèse d’acides alkyl-8 oxo-5 dihydro-5.8 pyrido-[2.3-d] pyrimidine-6 carboxyliques. C R Acad Sci [C] 278:717

    CAS  Google Scholar 

  • Pesson M, Antoine M, Chabassier S, Geiger S, Girard P, Richer D, de Lajudie P, Horvath E, Leriche B, Patte S (1974c) Antibactériens dérivés des acides alkyl-8 oxo-5 dihydro-5,8 pyrido [2,3-d] pyrimidine-6 carboxyliques. II. Dérivés pipérazinyl-2 et (alkyl-4 pipérazinyl)-2. Eur J Med Chem Chim Ther 9:591

    CAS  Google Scholar 

  • Pesson M, de Lajudie P, Antoine M, Girard P, Chabassier S (1975) Synthèse d’acides alkyl-1 oxo-4 dihydro-1,4 benzo [h] naphtyridine-1.6 carboxyliques-3 à action antibactérienne. C R Acad Sci [C] 280:1385

    CAS  Google Scholar 

  • Pesson M, de Lajudie P, Antoine M, Chabassier S, Girard P (1976) Acides alkyl-1 oxo- 4 dihydro-1,4 pyrido [2.3-b]quinoxaline-3 carboxyliques à action antibactérienne. C R Acad Sci [C] 282:861

    CAS  Google Scholar 

  • Pesson M, Antoine M, Benichon J-L, de Lajudie P, Horvath E, Leriche B, Patte S (1980) Antibactériens de synthèse — dérivés des acides pyrido (2,3-e) as.triazine-7 carboxyliques. Eur J Med Chem 15:269

    CAS  Google Scholar 

  • Petersen U, Grohe K, Zeiler H-J, Metzger K (1986) European patent 167 763 (04.06.1984), Bayer AG. Chem Abstr 104:186447v

    Google Scholar 

  • Petersen U, Grohe K, Schriewer M, Schenke T, Haller I, Metzger K, Endermann R, Zeiler H-J (1989) DOS 3 711 193 (02.04.1987), Bayer AG. Chem Abstr 110:114697c

    Google Scholar 

  • Petersen U, Schenke T, Krebs A, Grohe K, Schriewer M, Haller I, Metzger KG, Endermann R, Zeiler HJ (1988) Bayer AG, EP 350 733

    Google Scholar 

  • Petersen U, Krebs A, Schenke T, Grohe K, Schriewer M, Haller I, Metzger K, Endermann R, Zeiler H-J (1991) European patent 401 623 (07.06.1989),Bayer AG. Chem Abstr 114:207234x

    Google Scholar 

  • Petersen U, Krebs A, Schenke T, Philipps T, Grohe K, Bremm KD, Endermann R, Metzger KG, Haller I (1992) Bayer AG, EP 550 903; Chem Abstr 120:8616x

    Google Scholar 

  • Price CC, Roberts RM (1946) The synthesis of 4-hydroxyquinolines. I. Through ethoxymethylenemalonic ester. J Am Chem Soc 68:1204

    Article  PubMed  CAS  Google Scholar 

  • Prudchenko AT, Shchegoleva GS, Barkhash VA, Vorozhtsov NN Jr (1967) Some reactions of pentafluorobenzoylacetic ester. Zh Obshch Khim 37:2366

    Google Scholar 

  • Prudchenko AT, Shchegoleva GS, Barkhash VA, Vorozhtsov NN Jr (1968) Reactions of ethyl pentafluorobenzoylacetate. Chem Abstr 69:36059q

    Google Scholar 

  • Radi S, Hradil P (1991) Synthesis of some l-alkyl-l,4-dihydro-4-oxo-l,7- naphthyridine-3-carboxylic acids. Collect Czech Chem Commun 56:2420

    Article  Google Scholar 

  • Radi S, Zikan V (1989) Synthesis and antimicrobial activity of some 3-oxo-3H- pyrido[3,2,1-kl]phenoxazine-2-carboxylic acids. Collect Czech Chem Commun 54:506

    Article  Google Scholar 

  • Radi S, Zikan V (1989) Synthesis of some l-aryl-l,4-dihydro-4-oxoquinoline-3- carboxylic acids and their antibacterial activity. Collect Czech Chem Commun 54:2181

    Article  Google Scholar 

  • Radi S, Houskova V, Zikan V (1988) Priprava nekterych nekondenzovanych derivatu l,4-dihydro-4-oxo-3-pyridin-A 3-pyridazinkarboxylove kyseliny jako potencialnich antimikrobialne ucinnych latek. Cesk Farm 37:71

    Google Scholar 

  • Radi S, Houskova V, Zikan V (1989) Priprava substituovanych l,6-difenyl-l,4-dihydro- 4-oxo-3-pyridazinkarboxylovych kyselin. Cesk Farm 38:114

    Google Scholar 

  • Radi S, Moural J, Bendova R (1990) Synthesis and antibacterial activity of some l-aryl-l,4-dihydro-4-oxocinnoline-3-carboxylic acids. Collect Czech Commun 55:1311

    Article  Google Scholar 

  • Radi S, Kovarova L, Moural J, Bendova R (1991) Structural modification and new methods for preparation of ofloxacin analogs. Collect Czech Commun 56:1937

    Article  Google Scholar 

  • Remuzon P, Bouzard D, Di Cesare P, Essiz M, Jacquet JP, Kiechel JR, Ledonssal B, Kessler RE, Fung-Tome J (1991) Fluoronaphthyridines and quinolones as antibacterial agents. 3. Synthesis and structure-activity relationships of new 1-(1,1- dimethyl-2-fluoroethyl), l-[l-methyl-l-(fiuoromethyl)-2-fiuoroethyl], and 1-[1,1- (difluoromethyl)-2-fluoroethyl] substituted derivatives. J Med Chem 54:29

    Article  Google Scholar 

  • Remuzon P, Bouzard D, Di Cesare P, Dussy C, Jacquet J-P, Jaegly A (1992) Synthesis and antibacterial activity of new 5-substituted l-cyclopropyl-6-fluoro-7- piperazinyl-l,4-dihydro-4-oxo-l,8-naphthyridine-3-carboxylic acids. J Heterocycl Chem 29:985

    Article  CAS  Google Scholar 

  • Rohlfing SR, Gerster JF, Kvam DC (1976) Bioevaluation of the antibacterial flumequine for urinary tract use. Antimicrob Agents Chemother 10:20

    PubMed  CAS  Google Scholar 

  • Rufer C, Schwarz K (1977) Untersuchungen über die antibakterielle Aktivität von Chinoloncarbonsäuren. VII (1). Azaanaloga. In 2-Position durch Pyrazole substituierte 8-Äthyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidin-6-carbonsäuren. Eur J Med Chem Chim Ther 12:236

    CAS  Google Scholar 

  • Sanchez JP, Ashok K, Trehan K, Nichols JB (1987) The synthesis of a pyrido[2,3- c]pyridazine: a cinnoline related to 6-fluoronalidixic acid. J Heterocycl Chem 24:55

    Article  CAS  Google Scholar 

  • Sanchez JP, Bridges AJ, Busch R, Domagala JM, Gogliotti RD, Hagen SE, Heifetz CL, Joannides ET, Sesnie JC, Shapiro MA, Szotek DL (1992) New 8- (trifluoromethyl)-substituted quinolones. The benefits of the 8-fiuoro group with reduced phototoxic risk. J Med Chem 35:361

    Article  PubMed  CAS  Google Scholar 

  • Sandison AA, Tennant G (1974) A new heterocyclisation reaction leading to cinnolin- 4(lH)-one derivatives. J Chem Soc Chem Commun 752

    Google Scholar 

  • Santilli AA, Wanser SV, Kim DH, Scotese AC (1975) Synthesis of 5,6,7,8-tetrahydro- 5-oxopyrido[2,3-d]pyrimidine-6-carbonitriles and -6-carboxylic acid esters. J Heterocycl Chem 12:311

    Article  CAS  Google Scholar 

  • Sato K, Matsuura Y, Inoue M, Une T, Osada Y, Ogawa Y, Ogawa H, Mitsuhashi S (1982) In vitro and in vivo activity of DL-8280, a new oxazine derivative. Antimicrob Agents Chemother 22:548

    PubMed  CAS  Google Scholar 

  • Sauter F, Jordis U, Tanyolac S, Martinek P (1988a) Thieno[3,2-g]chinolin- und [1] Benzothieno-[5,6,7-ij]chinolizincarbonsäurederivate. Arch Pharm (Weinheim) 321:241

    Article  CAS  Google Scholar 

  • Sauter F, Jordis U, Tanyolac S (1988b) Synthesen neuer Chinolon-Chemothera- peutika, 3. Mitt. Sci Pharm 56:73

    CAS  Google Scholar 

  • Sauter F, Jordis U, Martinek P (1989) Synthesis of novel quinolone-type drugs. Part 4. Pyrido[3,2,1-gh][l,7]phenanthroline- and benzo[i,j]quinolizine-carboxylic acids. Sci Pharm 57:7

    CAS  Google Scholar 

  • Sawa Y, Kato T, Masuda T, Hori M, Fujimora H (1975) Studies on the syntheses of analgesics. IV. Syntheses of l,2,3,4-tetrahydro-5H-benzazepine derivatives. Chem Pharm Bull (Tokyo) 23:1917

    Article  CAS  Google Scholar 

  • Scheer M (1987a) Studies on the antibacterial activity of Baytril. Vet Med Rev 2:90

    Google Scholar 

  • Scheer M (1987b) Concentrations of active ingredient in the serum and in tissues after oral and parenteral administration of Baytril. Vet Med Rev 2:104

    Google Scholar 

  • Schofield K, Simpson JCE (1945) Cinnolines. III. The Richter reaction. J Chem Soc 512

    Google Scholar 

  • Schriewer M, Grohe K (1988) DOS 3 615 767 (10.05.1986), Bayer AG. Chem Abstr 108:94416p

    Google Scholar 

  • Schriewer M, Grohe K, Zeiler H-J, Metzger K (1987a) DOS 3 543 513 (10.12.1985), Bayer AG. Chem Abstr 107:154342c

    Google Scholar 

  • Schriewer M, Grohe K, Zeiler H-J, Metzger K (1987b) DOS 3 600 891 (15.01.1986), Bayer AG. Chem Abstr 107:198345k

    Google Scholar 

  • Schriewer M, Grohe K, Zeiler H-J, Metzger K (1987c) DOS 3 509 546 (16.03.1985), Bayer AG. Chem Abstr 106:4900y

    Google Scholar 

  • Schriewer M, Grohe K, Hagemann H, Zeiler H-J, Metzger K (1988a) DOS 3 623 757 (15.07.1986), Bayer AG. Chem Abstr 109:86326q

    Google Scholar 

  • Schriewer M, Grohe K, Petersen U, Haller I, Metzger K, Endermann R, Zeiler H-J (1988b) DOS 3 702 393 (28.01.1987), Bayer AG. Chem Abstr 109:230824v

    Google Scholar 

  • Schroeder MC, Kiely JS (1988) Synthesis of a novel tricyclic 4-quinolone. Incorporation of a spirb-cyclopropyl group at N1 by bridging to C2. J Heterocycl Chem 25:1796

    Article  Google Scholar 

  • Schwan TJ, Freedman R, Pollack JR (1983) Synthesis, structure elucidation and antibacterial activity of 6-ethyl-6,9-dihydro-9-oxopyrazolo[3,4-f]quinoline-8- carboxylic acid. J Heterocycl Chem 20:1351

    Article  CAS  Google Scholar 

  • Segawa J, Kitano M, Kazuno K, Tsuda M, Shirahase I, Ozaki M, Matsuda M, Kise M (1992a) Studies on pyridonecarboxylic acids [1]. 2. Synthesis and antibacterial activity of 8-substituted 7-fluoro-5-oxo-5H-thiazolo[3,2-a] quinoline-4-carboxylic acids. J Heterocycl Chem 29:1117

    Article  CAS  Google Scholar 

  • Segawa J, Kitano M, Kazuno K, Matsuoka M, Shirahase I, Ozaki M, Matsuda M, Tomii Y, Kise M (1992b) Studies on pyridonecarboxylic acids. 1. Synthesis and antibacterial evaluation of 7-substituted-6-halo-4-oxo-4H-[l,3] thiazeto[3,2-a] quinoline- 3-carboxylic acids. J Med Chem 35:4727

    Article  PubMed  CAS  Google Scholar 

  • Shoup RR, Castle RN (1965) Cinnoline chemistry. XI. The ultraviolet spectra of halogen substituted 4-hydroxy- and 4-mercaptocinnolines. J Heterocycl Chem 2:63

    Article  CAS  Google Scholar 

  • Singh B (1991) Synthesis of 2-aza analog of rosoxacin. J Heterocycl Chem 28:881

    Article  CAS  Google Scholar 

  • Staiger RP, Miller EB (1959) Isatoic anhydride. IV. Reactions with various nucleo- philes. J Org Chem 24:1214

    Article  CAS  Google Scholar 

  • Stanovnik B, Tisler M (1974) Convenient cyclization of o-difunctional heterocycles with N,N-dimethylformamide dimethyl acetal. Synthesis 120

    Google Scholar 

  • Stefancich G, Artico M, Corelli F, Massa S, Panico S, Simonetti N (1985) l-ethyl-6- fluoro-l,4-dihydro-4-oxo-7-(lH-pyrrol-l-yl)-quinoline-3-carboxylic acid, a new fluorinated compound of oxacin family with high broad-spectrum antibacterial activities. Farmaco [Sci] 40:237

    CAS  Google Scholar 

  • Strehlke P (1977) Untersuchungen über die antibakterielle Aktivität von Chinoloncarbonsäuren. VIII (1) Azaanaloga. Eine neue Synthese antibak- teriell wirksamer 1,7-disubstituierter l,4-Dihydro-4-oxo-l,6-naphthyridin-3- carbonsäuren. Eur J Med Chem Chim Ther 12:541

    CAS  Google Scholar 

  • Suzuki N, Tanaka Y, Dohmori R (1979) Synthesis of antimicrobial agents. I. Synthesis and antimicrobial activities of thiazoloquinoline derivatives. Chem Pharm Bull (Tokyo) 27:1

    Article  CAS  Google Scholar 

  • Taguchi M, Kondo H, Inoue Y, Kawahata Y, Jinbo Y, Sakamoto F, Tsukamoto G (1992) Synthesis and antibacterial activity of new tetracyclic quinolone antibacte- rials. J Med Chem 35:94

    Article  PubMed  CAS  Google Scholar 

  • Taylor EC, Heindel ND (1967) Cyclizations of anthranilate-acetylenedicarboxylate adducts. A facile route to 2,8-dicarboalkoxy-4(lH)-quinolinones. J Org Chem 32:3339

    Article  CAS  Google Scholar 

  • Terni P, Rugarli PL, Maiorana S, Pagella PG, Fusco R (1988) European patent 252,352 (01.07.1986), Mediolanum Farm. Chem Abstr 109:129034n

    Google Scholar 

  • Todo Y, Yamafuji T, Nagumo K, Kitayama I, Nagaki H, Miyajima M, Konishi Y, Narita H, Takano S, Seikawa I (1987) DOS 3 601 517 (20.01.1986). Toyama Chem. Chem Abstr 107:77777u

    Google Scholar 

  • Toja E, Kettenring J, Goldstein B, Tarzia G (1986a) Pyrrolopyridine analogs of nalidixic acid. 2. Pyrrolo[3,4-b]pyridines. J Heterocycl Chem 23:1561

    Google Scholar 

  • Toja E, Tarzia G, Ferrari P, Tuan G (1986b) Pyrrolopyridine analogs of nalidixic acid. 1. Pyrrolo [2,3-b] pyridines. J Heterocycl Chem 23:1555

    Article  CAS  Google Scholar 

  • Von Liebig J (1853) Ueber Kynurensäure. Ann Chem 86:125

    Article  Google Scholar 

  • Von Liebig J (1858) Ueber Kreatin und Kynurensäure im Hundeharn. Ann Chem 108:354

    Article  Google Scholar 

  • Von Richter V (1883) Ueber Cinnolinderivate. Chem Ber 16:677

    Article  Google Scholar 

  • Wentland MP, Lesher GY, Reumann M, Gruett MD, Singh B, Aldous SC, Dorff PH, Rake JB, Coughlin SA (1993) Mammalian topoisomerase II inhibitory activity of l-cyclopropyl-6,8-difluoro-l,4-dihydro-7-(2,6-dimethyl-4-pyridinyl)-4-oxo-3- quinolinecarboxylic acid and related derivatives. J Med Chem 36:2801

    Article  PubMed  CAS  Google Scholar 

  • White WA (1970) DOS 2 005 104 (06.08.1970), Eli Lilly & Co. Chem Abstr 73:77269j

    Google Scholar 

  • Wick AE (1979) DOS 2 901 868 (18.01.1978), Hoffmann-La Roche. Chem Abstr 91:211273h

    Google Scholar 

  • Xiao W, Krishnan R, Lin Y-I, Delos Santos EF, Kuck NA, Babine RE, Lang SA Jr (1989) Synthesis and in vitro antibacterial activity of some 1- (difluoromethoxyphenyl)quinolone-3-carboxylic acids. J Pharm Sci 78:585

    Article  PubMed  CAS  Google Scholar 

  • Zeiler H-J, Grohe K (1984) The in vitro and in vivo activity of ciprofloxacin. Eur J Clin Microbiol 3:339

    Article  PubMed  CAS  Google Scholar 

  • Zhang MQ, Haemers A, Vanden Berghe D, Pattyn SR, Bollaert W (1991) Quinolone antibacterials. 2. 6-substituted-7-(2-thiazolyl and thiazolidinyl)quinolones. J Heterocycl Chem 28:685

    Article  CAS  Google Scholar 

  • Ziegler CB Jr, Moran DB, Fenton TJ, Lin Y-I (1990) The Synthesis and biological activity of 8-fluoro-9-(4-methyl-l-piperazinyl)-6-oxo-6H-benzo[c]quinolizine-5- carboxylic acid. J Heterocycl Chem 27:587

    Article  CAS  Google Scholar 

Download references

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1998 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Grohe, K. (1998). The Chemistry of the Quinolones: Methods of Synthesizing the Quinolone Ring System. In: Kuhlmann, J., Dalhoff, A., Zeiler, HJ. (eds) Quinolone Antibacterials. Handbook of Experimental Pharmacology, vol 127. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-80364-2_2

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-80364-2_2

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-80366-6

  • Online ISBN: 978-3-642-80364-2

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics