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【结 构 式】 
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【分子编号】33463 【品名】2-bromoethyl acetate 【CA登记号】927-68-4 |
【 分 子 式 】C4H7BrO2 【 分 子 量 】167.00238 【元素组成】C 28.77% H 4.22% Br 47.85% O 19.16% |
合成路线1
该中间体在本合成路线中的序号：(B)Compound can be prepared in two similar ways both starting from 7-chloro-1,3-dihydro-5-(o-fluorophenyl)-2H-1,4-benzodiazepin-2-one-4-oxide (I): 1) The condensation of (I) with 2-bromoethanol (A) by means of NaH in DMF gives the N-hydroxyethyl derivative (II), which by refluxing with acetic anhydride is converted into 7-chloro-1,3-dihydro-1-(2-acetoxyethyl)-3-acetoxy-5-(o-fluorophenyl)-2H-1,4-benzodiazepin-2-one (III). Finally, (III) is deacetylated with methanolic ammonia. 2) The condensation of (I) with 2-bromoethylacetate (B) as before gives the N-acetoxyethyl derivative (IV), which by refluxing with acetic anhydride is converted into (III).
| 【1】 Tamagnone, G.F.; et al.; A new benzodiazepine: 1-(2-hydroxyethyl)-3-hydroxy-7-chloro-1,3-dihydro-5-(o-fluorophenyl)-2H-1,4-benzodiazepine-2-one. J Pharm Pharmacol 1974, 26, 566. |
| 【2】 De Marchi, F.; Tamagnone, G.F.; Benzodiazepine compounds for therapeutical use. DE 2338058; ES 405260; FR 2194432; GB 1431282; JP 49080086 . |
| 【3】 Tamagnone, G.F.; et al.; A new series of benzodiazepines: 1-Hydroxyalkyl derivatives of 1,3-dihydro-2H-1,4-benzodiazepin-2-one. Arzneim-Forsch Drug Res 1975, 25, 5, 720-722. |
| 【4】 de Angelis, L.; Castaner, J.; SAS-643. Drugs Fut 1978, 3, 2, 145. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 10059 | Ethylene bromohydrin; 2-Bromo-1-ethanol | 540-51-2 | C2H5BrO | 详情 | 详情 |
| (B) | 33463 | 2-bromoethyl acetate | 927-68-4 | C4H7BrO2 | 详情 | 详情 |
| (I) | 33459 | 7-chloro-5-(2-fluorophenyl)-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-4-ium-4-olate | C15H10ClFN2O2 | 详情 | 详情 | |
| (II) | 33460 | 7-chloro-5-(2-fluorophenyl)-1-(2-hydroxyethyl)-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-4-ium-4-olate | C17H14ClFN2O3 | 详情 | 详情 | |
| (III) | 33461 | 2-[3-(acetoxy)-7-chloro-5-(2-fluorophenyl)-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-1-yl]ethyl acetate | C21H18ClFN2O5 | 详情 | 详情 | |
| (IV) | 33462 | 1-[2-(acetoxy)ethyl]-7-chloro-5-(2-fluorophenyl)-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-4-ium-4-olate | C19H16ClFN2O4 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(IX)Chlorination of 5-amino-2,4,6-triiodoisophthalic acid (I) with SOCl2 in EtOAc or toluene affords acid chloride (II). Yields have been improved with the addition of benzyltriethylammonium chloride as a catalyst. Acid chloride (II) is then condensed with 3-amino-1,2-propanediol (III) to produce diamide (IV). Compound (IV) is converted to the tetraacetate ester (V) employing acetic anhydride in pyridine. Subsequent acylation of the amino group of (V) with acetoxyacetyl chloride (VI) gives amide (VII). After saponification of the ester groups of (VII), the resultant hydroxy acetamide (VIII) is alkylated by 2-chloroethanol (IX) to furnish the title compound. Alternatively, amide (VIII) is alkylated by bromoethyl acetate (X), producing (XI). Hexa-ester (XI) is finally hydrolyzed with aqueous sulfuric acid. An improved procedure for this final hydrolysis step uses 1,1,2-trichloroethane as co-solvent.
| 【1】 Lin, Y. (Mallinckrodt Medical Inc.); Cpds. suitable for X-ray visualisation methods. EP 0083964; US 4396598 . |
| 【2】 Dunn, T.J.; White, D.H.; Kneller, M.T.; Jones, M.M.; Doran, N.O. III; Bailey, A.R. (Mallinckrodt Medical Inc.); Process for producing ioversol. WO 9727172 . |
| 【3】 Kneller, M.T.; Bailey, A.R.; Sathe, S.S.; Spears, A.T.; Wisneski, R.C. (Mallinckrodt Medical Inc.); Improved synthesis of ioversol. WO 9323365 . |
| 【4】 Villa, M.; Castaldi, G.; Pozzoli, C.; Russo, L. (Zambon Group SpA); Process for the preparation of 5-amino-2,4,6-triiodoisophthalic acid dichloride by chlorination with thionyl chloride in the presence of a catalyst. WO 9636590 . |
| 【5】 Lin, Y.; Dean, R.T.; Kneller, M.; Wallace, R.A.; McCarthy, W.Z.; White, D.H. (Mallinckrodt Medical Inc.); Process for production of ioversol. WO 9111431 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 22006 | 5-amino-2,4,6-triiodoisophthalic acid | 35453-19-1 | C8H4I3NO4 | 详情 | 详情 |
| (II) | 31194 | 5-amino-2,4,6-triiodoisophthaloyl dichloride | 37441-29-5 | C8H2Cl2I3NO2 | 详情 | 详情 |
| (III) | 12979 | 3-Amino-1,2-propanediol；3-aminopropane-1,2-diol | 616-30-8 | C3H9NO2 | 详情 | 详情 |
| (IV) | 59316 | 5-amino-N~1~,N~3~-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide | C14H18I3N3O6 | 详情 | 详情 | |
| (V) | 59322 | 2-(acetyloxy)-1-({[3-amino-5-({[2,3-bis(acetyloxy)propyl]amino}carbonyl)-2,4,6-triiodobenzoyl]amino}methyl)ethyl acetate | C22H26I3N3O10 | 详情 | 详情 | |
| (VI) | 10456 | Acetoxiacetil chloride; 2-chloro-2-oxoethyl acetate | 13831-31-7 | C4H5ClO3 | 详情 | 详情 |
| (VII) | 59323 | 2-(acetyloxy)-1-({[3-{[2-(acetyloxy)acetyl]amino}-5-({[2,3-bis(acetyloxy)propyl]amino}carbonyl)-2,4,6-triiodobenzoyl]amino}methyl)ethyl acetate | C26H30I3N3O13 | 详情 | 详情 | |
| (VIII) | 59324 | N~1~,N~3~-bis(2,3-dihydroxypropyl)-5-(glycoloylamino)-2,4,6-triiodoisophthalamide | C16H20I3N3O8 | 详情 | 详情 | |
| (IX) | 33463 | 2-bromoethyl acetate | 927-68-4 | C4H7BrO2 | 详情 | 详情 |
| (X) | 10384 | 2-Chloro-1-ethanol; Ethylene chlorohydrin | 107-07-3 | C2H5ClO | 详情 | 详情 |
| (XI) | 59325 | 2-[[2-(acetyloxy)acetyl]-3,5-bis({[2,3-bis(acetyloxy)propyl]amino}carbonyl)-2,4,6-triiodoanilino]ethyl acetate | C30H36I3N3O15 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(IV)In an alternative procedure, the intermediate amino tetraacetate (I) is acylated by chloroacetyl chloride (II), yielding chloroacetamide (III). The amide N is then alkylated with bromoethyl acetate (IV) to produce (V). Simultaneous hydrolysis of the acetate esters and the chloro group in aqueous sulfuric acid furnishes the title compound.
| 【1】 McCarthy, W.Z.; Kneller, M.T.; Lin, Y.; White, D.H. (Mallinckrodt Medical Inc.); Synthesis of ioversol using chloroacetyl chloride. WO 9301840 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 59322 | 2-(acetyloxy)-1-({[3-amino-5-({[2,3-bis(acetyloxy)propyl]amino}carbonyl)-2,4,6-triiodobenzoyl]amino}methyl)ethyl acetate | C22H26I3N3O10 | 详情 | 详情 | |
| (II) | 11296 | 2-Chloroacetyl chloride; Chloroacetic chloride | 79-04-9 | C2H2Cl2O | 详情 | 详情 |
| (III) | 59328 | 2-(acetyloxy)-1-[({3-({[2,3-bis(acetyloxy)propyl]amino}carbonyl)-5-[(2-chloroacetyl)amino]-2,4,6-triiodobenzoyl}amino)methyl]ethyl acetate | C24H27ClI3N3O11 | 详情 | 详情 | |
| (IV) | 33463 | 2-bromoethyl acetate | 927-68-4 | C4H7BrO2 | 详情 | 详情 |
| (V) | 59329 | 2-(acetyloxy)-1-({[3-[[2-(acetyloxy)ethyl](2-chloroacetyl)amino]-5-({[2,3-bis(acetyloxy)propyl]amino}carbonyl)-2,4,6-triiodobenzoyl]amino}methyl)ethyl acetate | C28H33ClI3N3O13 | 详情 | 详情 |
合成路线4
该中间体在本合成路线中的序号：(IV)Similarly, the tetrahydroxy amine (I) is acylated by chloroacetyl chloride (II) to produce the tetraester amide (III). After amide alkylation with bromoethyl acetate (IV), the resultant penta-ester (V) is hydrolyzed to the title compound using aqueous sulfuric acid.
| 【1】 McCarthy, W.Z.; Kneller, M.T.; Lin, Y.; White, D.H. (Mallinckrodt Medical Inc.); Synthesis of ioversol using chloroacetyl chloride. WO 9301840 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 59316 | 5-amino-N~1~,N~3~-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide | C14H18I3N3O6 | 详情 | 详情 | |
| (II) | 11296 | 2-Chloroacetyl chloride; Chloroacetic chloride | 79-04-9 | C2H2Cl2O | 详情 | 详情 |
| (III) | 59326 | 2-({3-[({2,3-bis[(2-chloroacetyl)oxy]propyl}amino)carbonyl]-5-[(2-chloroacetyl)amino]-2,4,6-triiodobenzoyl}amino)-1-{[(2-chloroacetyl)oxy]methyl}ethyl 2-chloroacetate | C24H23Cl5I3N3O11 | 详情 | 详情 | |
| (IV) | 33463 | 2-bromoethyl acetate | 927-68-4 | C4H7BrO2 | 详情 | 详情 |
| (V) | 59330 | 2-({3-[[2-(acetyloxy)ethyl](2-chloroacetyl)amino]-5-[({2,3-bis[(2-chloroacetyl)oxy]propyl}amino)carbonyl]-2,4,6-triiodobenzoyl}amino)-1-{[(2-chloroacetyl)oxy]methyl}ethyl 2-chloroacetate | C28H29Cl5I3N3O13 | 详情 | 详情 |
合成路线5
该中间体在本合成路线中的序号：(IV)A further synthetic variation for the title compound is based on the acylation of intermediate (I) with acetoxyacetyl chloride (II) to afford (III). Amide alkylation with bromoethyl acetate (IV) furnishes (V). The ester groups of (V) are finally hydrolyzed in aqueous sulfuric acid.
| 【1】 Lin, Y.; Wallace, R.A.; McCarthy, W.Z.; Kneller, M.T.; White, D.H. (Mallinckrodt Medical Inc.); Synthesis of ioversol using a minimal excessof acetoxyacetylchloride. US 5371278 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 59316 | 5-amino-N~1~,N~3~-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide | C14H18I3N3O6 | 详情 | 详情 | |
| (II) | 10456 | Acetoxiacetil chloride; 2-chloro-2-oxoethyl acetate | 13831-31-7 | C4H5ClO3 | 详情 | 详情 |
| (III) | 59331 | 2-[(3-{[2-(acetyloxy)acetyl]amino}-5-{[(2,3-bis{[2-(acetyloxy)acetyl]oxy}propyl)amino]carbonyl}-2,4,6-triiodobenzoyl)amino]-1-({[2-(acetyloxy)acetyl]oxy}methyl)ethyl 2-(acetyloxy)acetate | C34H38I3N3O21 | 详情 | 详情 | |
| (IV) | 33463 | 2-bromoethyl acetate | 927-68-4 | C4H7BrO2 | 详情 | 详情 |
| (V) | 59332 | 2-[(3-{[2-(acetyloxy)acetyl][2-(acetyloxy)ethyl]amino}-5-{[(2,3-bis{[2-(acetyloxy)acetyl]oxy}propyl)amino]carbonyl}-2,4,6-triiodobenzoyl)amino]-1-({[2-(acetyloxy)acetyl]oxy}methyl)ethyl 2-(acetyloxy)acetate | C38H44I3N3O23 | 详情 | 详情 |
合成路线6
该中间体在本合成路线中的序号：(XVIII)Alternatively, (+)-(XVII) can be obtained as follows: Treatment of (X) with 1-acetoxy-2-bromoethane (XVIII) in DMF in the presence of NaHCO3 yields derivative (XIX), which is then chlorinated by means of SO2Cl2 in CH2Cl2 to provide (XX). Simultaneous hydrolysis and intramolecular cyclization of (XX) by means of Et3N /H2O in THF affords (XXI), which is then converted into butyl ester derivative (XXII) by treatment with refluxing butanol (B). Resolution of the racemic mixture (XXII) by treatment with Lipase PL in vinyl acetate followed by chromatographic separation provides alcohol (-)-(XXIII) and acetoxy (+)-(XXIV). Hydrolysis of (+)-(XXIV) with hot H2SO4/EtOH gives alcohol (+)-(XXV), which is then condensed with 1-methylpiperazine (XVI) in DMF to yield derivative (+)-(XXVI). Finally, treatment with (diethylamino)sulfur trifluoride (DAST) in CH2Cl2 provides fluoro derivative (+)-(XVII). Alternatively, (+)-(XXV) can be obtained by conversion of (XXI) into octyl ester (XXVII) by means of refluxing octanol (A), followed by its enantiomer enzymatic resolution with Liposyme IM in vinyl acetate and chromatographic separation to afford (-)-(XXVIII) and (+)-(XXIX). Finally, hydrolysis of (+)-(XXIX) with hot H2SO4/EtOH yields (+)-(XXV). An analogous procedure comprising enantiomer separation and subsequent hydrolysis can be performed from ethyl esters (XX) or (XXI) by treatment with the corresponding lipases in an appropriate solvent.
| 【1】 Segawa, J.; Matsuoka, M.; Tomii, Y. (Nippon Shinyaku Co., Ltd.); Quinolinecarboxylic acid deriv. and process for producing the same. EP 0675127; WO 9414819 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 24543 | vinyl acetate | 108-05-4 | C4H6O2 | 详情 | 详情 | |
| (A) | 12970 | (8R,9S,10R,13S,14R)-14-Hydroxy-3-methoxy-10,13-dimethyl-1,2,7,8,9,10,11,12,13,14,15,16-dodecahydro-17H-cyclopenta[a]phenanthren-17-one | C20H28O3 | 详情 | 详情 | |
| (B) | 29766 | butanol; n-butanol; 1-butanol | 71-36-3 | C4H10O | 详情 | 详情 |
| (X) | 42956 | ethyl 4-(benzoyloxy)-6,7-difluoro-2-sulfanyl-3-quinolinecarboxylate | C19H13F2NO4S | 详情 | 详情 | |
| (XVI) | 10061 | 1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine | 109-01-3 | C5H12N2 | 详情 | 详情 |
| (XVII) | 42961 | ethyl (1R)-6-fluoro-1-(fluoromethyl)-7-(4-methyl-1-piperazinyl)-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate | C19H21F2N3O3S | 详情 | 详情 | |
| (XVIII) | 33463 | 2-bromoethyl acetate | 927-68-4 | C4H7BrO2 | 详情 | 详情 |
| (XIX) | 42962 | ethyl 2-[[2-(acetoxy)ethyl]sulfanyl]-4-(benzoyloxy)-6,7-difluoro-3-quinolinecarboxylate | C23H19F2NO6S | 详情 | 详情 | |
| (XX) | 42963 | ethyl 2-[[2-(acetoxy)-1-chloroethyl]sulfanyl]-4-(benzoyloxy)-6,7-difluoro-3-quinolinecarboxylate | C23H18ClF2NO6S | 详情 | 详情 | |
| (XXI) | 42964 | ethyl 1-[(acetoxy)methyl]-6,7-difluoro-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate | C16H13F2NO5S | 详情 | 详情 | |
| (XXII) | 42965 | butyl 6,7-difluoro-1-(hydroxymethyl)-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate | C16H15F2NO4S | 详情 | 详情 | |
| (XXIII) | 42966 | butyl (1S)-6,7-difluoro-1-(hydroxymethyl)-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate | C16H15F2NO4S | 详情 | 详情 | |
| (XXIV) | 42967 | butyl (1R)-1-[(acetoxy)methyl]-6,7-difluoro-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate | C18H17F2NO5S | 详情 | 详情 | |
| (XXV) | 42968 | ethyl (1R)-6,7-difluoro-1-(hydroxymethyl)-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate | C14H11F2NO4S | 详情 | 详情 | |
| (XXVI) | 42969 | ethyl (1R)-6-fluoro-1-(hydroxymethyl)-7-(4-methyl-1-piperazinyl)-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate | C19H22FN3O4S | 详情 | 详情 | |
| (XXVII) | 42971 | octyl 2-[6,7-difluoro-1-(hydroxymethyl)-4-oxo-4H-[1,3]thiazeto[3,2-a]quinolin-3-yl]acetate | C21H25F2NO4S | 详情 | 详情 | |
| (XXVIII) | 42972 | octyl 2-[(1S)-1-[(acetoxy)methyl]-6,7-difluoro-4-oxo-4H-[1,3]thiazeto[3,2-a]quinolin-3-yl]acetate | C23H27F2NO5S | 详情 | 详情 | |
| (XXIX) | 42973 | octyl 2-[(1R)-6,7-difluoro-1-(hydroxymethyl)-4-oxo-4H-[1,3]thiazeto[3,2-a]quinolin-3-yl]acetate | C21H25F2NO4S | 详情 | 详情 |
合成路线7
该中间体在本合成路线中的序号：(XVIII)Alternatively, (-)-(XVII) can be obtained as follows: Treatment of (X) with 1-acetoxy-2-bromoethane (XVIII) in DMF in the presence of NaHCO3 yields derivative (XIX), which is then chlorinated by means of SO2Cl2 in CH2Cl2 to provide (XX). Simultaneous hydrolysis and intramolecular cyclization of (XX) by means of Et3N /H2O in THF affords (XXI), which is then converted into octyl ester derivative (XXII) by treatment with refluxing octanol (A). Resolution of the racemic mixture (XXII) by treatment with Liposyme IM in vinyl acetate followed by chromatographic separation provides alcohol (+)-(XXIII) and acetoxy (-)-(XXIV). Hydrolysis of (-)-(XXIV) with hot H2SO4/EtOH gives alcohol (-)-(XXV), which then reacts with 1-methylpiperazine (XVI) in DMF to yield derivative (-)-(XXVI). Finally, treatment with (diethylamino)sulfur trifluoride (DAST) in CH2Cl2 provides fluoro derivative (-)-(XVII). Alternatively, (-)-(XXV) can be obtained by conversion of (XXI) into butyl ester (XXVII) by means of refluxing butanol (B), followed by its enantiomer enzymatic resolution with Lipase PL in vinyl acetate and chromatographic separation to afford (+)-(XXVIII) and (-)-(XXIX). Finally, hydrolysis of (-)-(XXIX) with hot H2SO4/EtOH yields (-)-(XXV). An analogous procedure comprising enantiomer separation and subsequent hydrolysis can be performed from ethyl esters (XX) or (XXI) by treatment with the corresponding lipases in an appropriate solvent.
| 【1】 Segawa, J.; Matsuoka, M.; Tomii, Y. (Nippon Shinyaku Co., Ltd.); Quinolinecarboxylic acid deriv. and process for producing the same. EP 0675127; WO 9414819 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 24543 | vinyl acetate | 108-05-4 | C4H6O2 | 详情 | 详情 | |
| (A) | 12970 | (8R,9S,10R,13S,14R)-14-Hydroxy-3-methoxy-10,13-dimethyl-1,2,7,8,9,10,11,12,13,14,15,16-dodecahydro-17H-cyclopenta[a]phenanthren-17-one | C20H28O3 | 详情 | 详情 | |
| (B) | 29766 | butanol; n-butanol; 1-butanol | 71-36-3 | C4H10O | 详情 | 详情 |
| (X) | 42956 | ethyl 4-(benzoyloxy)-6,7-difluoro-2-sulfanyl-3-quinolinecarboxylate | C19H13F2NO4S | 详情 | 详情 | |
| (XVI) | 10061 | 1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine | 109-01-3 | C5H12N2 | 详情 | 详情 |
| (XVII) | 42975 | ethyl (1S)-6-fluoro-1-(fluoromethyl)-7-(4-methyl-1-piperazinyl)-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate | C19H21F2N3O3S | 详情 | 详情 | |
| (XVIII) | 33463 | 2-bromoethyl acetate | 927-68-4 | C4H7BrO2 | 详情 | 详情 |
| (XIX) | 42962 | ethyl 2-[[2-(acetoxy)ethyl]sulfanyl]-4-(benzoyloxy)-6,7-difluoro-3-quinolinecarboxylate | C23H19F2NO6S | 详情 | 详情 | |
| (XX) | 42963 | ethyl 2-[[2-(acetoxy)-1-chloroethyl]sulfanyl]-4-(benzoyloxy)-6,7-difluoro-3-quinolinecarboxylate | C23H18ClF2NO6S | 详情 | 详情 | |
| (XXI) | 42964 | ethyl 1-[(acetoxy)methyl]-6,7-difluoro-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate | C16H13F2NO5S | 详情 | 详情 | |
| (XXII) | 42971 | octyl 2-[6,7-difluoro-1-(hydroxymethyl)-4-oxo-4H-[1,3]thiazeto[3,2-a]quinolin-3-yl]acetate | C21H25F2NO4S | 详情 | 详情 | |
| (XXIII) | 42973 | octyl 2-[(1R)-6,7-difluoro-1-(hydroxymethyl)-4-oxo-4H-[1,3]thiazeto[3,2-a]quinolin-3-yl]acetate | C21H25F2NO4S | 详情 | 详情 | |
| (XXIV) | 42972 | octyl 2-[(1S)-1-[(acetoxy)methyl]-6,7-difluoro-4-oxo-4H-[1,3]thiazeto[3,2-a]quinolin-3-yl]acetate | C23H27F2NO5S | 详情 | 详情 | |
| (XXV) | 42976 | ethyl (1S)-6,7-difluoro-1-(hydroxymethyl)-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate | C14H11F2NO4S | 详情 | 详情 | |
| (XXVI) | 42977 | ethyl (1S)-6-fluoro-1-(hydroxymethyl)-7-(4-methyl-1-piperazinyl)-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate | C19H22FN3O4S | 详情 | 详情 | |
| (XXVII) | 42965 | butyl 6,7-difluoro-1-(hydroxymethyl)-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate | C16H15F2NO4S | 详情 | 详情 | |
| (XXVIII) | 42967 | butyl (1R)-1-[(acetoxy)methyl]-6,7-difluoro-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate | C18H17F2NO5S | 详情 | 详情 | |
| (XXIX) | 42966 | butyl (1S)-6,7-difluoro-1-(hydroxymethyl)-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate | C16H15F2NO4S | 详情 | 详情 |