Quinolone- and naphthyridonecarboxylic acid derivatives

• Main Authors: UWE PETERSEN, KLAUS-DIETER BREMM, THOMAS SCHENKE
• Format: Patent
• Language: English
• Published: 10.07.1996
• Edition: 6
• Subjects: CHEMISTRY; HETEROCYCLIC COMPOUNDS; HUMAN NECESSITIES; HYGIENE; MEDICAL OR VETERINARY SCIENCE; METALLURGY; ORGANIC CHEMISTRY; PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES; SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS

7-(1,2,3,7a-Tetrahydroisoindol-2-yl)-4-quinolone (or naphthyridone)-3-carboxylic acid derivs. of formula T-Q (I) and their hydrates, acid addn. salts and alkali(ne earth) metal, silver and guanidinium salts are new. Pure diastereomers and enantiomers are included. Q = naphthyridine, quinoline or tricyclic analogue gp. of formula (Q1)-(Q3); R1 = 1-4C alkyl (opt. mono- or disubstd. by halogen or OH), 2-4C alkenyl, 3-6C cycloalkyl (opt. substd. by one or two F), bicyclo(1.1.1)pent-1-yl, 1,1-dimethylpropargyl, 3-oxetanyl, OMe, NH2, NHMe, NMe2 or phenyl (opt. mono- or disubstd. by halogen, NH2 or OH); R2 = OH, 1-3C alkoxy (opt. substd. by OH, OMe, NH2 or NMe2), benzyloxy, (5-methyl-2-oxo-1,3-dioxol-4-yl)methoxy, acetoxy-methoxy, pivaloyloxymethoxy, 5-indanyloxy, phthalidinyloxy, 3-acetoxy-2-oxobutoxy, CH2NO2, CH)COOMe)2 or CH)COOEt)2; R9 = H or 1-3C alkyl (opt. substd. by OMe, OH or halogen); R" = H, Me or CH2F; X = halogen or NO2; Y = H, halogen, NH2, OH, OMe, SH, Me , halomethyl or vinyl; A = N or CR7; R7 = H, halogen, CF3, OMe, OCHF2, Me, CN, vinyl or ethynyl; or R7+R1 = *OCH2CHMe, *SCH2CH2, *SCH2CHMe, *CH2CH2CHMe or *OCH2NR8, where * denotes the bond to A; R8 = H, Me or CHO; D = N or CR10; R10 = H, halogen, CF3, OMe, OCHF2 or Me; or R10+R9 = *OCH2, *NHCH2, *NMeCH2, *NEtCH2, *N(cyclopropyl)CH2 or *SCH2, where * denotes the bond to D; T = 1,2,3,7a-tetrahydroisoindol-2-yl gp. of formula (T); B = -(CH2)m-NR4R4 or -(CH2)m-OR5; m = 0 or 1; R3 = H, Me or (1-4C) alkoxycarbonyl; R4-R6 = H or Me. Also claimed are 18 intermediate hexa- or tetra-hydroisoindole derivs.