发明名称 Azide substituted naphthylene or rylene imide derivatives and their use as reagents in click-reactions
摘要 Novel mono-azide substituted rylene-imide derivatives, their use in methods for the detection of analytes and reagents kits for the detection of analytes comprising said novel mono-azide substituted rylene-imide derivatives.
申请公布号 US8921558(B2) 申请公布日期 2014.12.30
申请号 US201314084851 申请日期 2013.11.20
申请人 BASF SE 发明人 Gessner Thomas;Reichelt Helmut;Münster Ingo;Könemann Martin;Pschirer Neil Gregory;Qu Jianqiang;Sens Rüdiger;Schwögler Anja;Manetto Antonio
分类号 C07D221/06;G01N21/76;C07D221/14;C12Q1/68;C07D221/18;C07D471/06 主分类号 C07D221/06
代理机构 Drinker Biddle & Reath LLP 代理人 Drinker Biddle & Reath LLP
主权项 1. A substituted naphthylene or rylene imide derivative of the general formula Iin which the variables are each defined as follows: Y one of the two radicals is a radical of the formula (y1) -L-Z—R1  (y1)and the other radical in each case is hydrogen; R are identical or different radicals: aryloxy, arylthio, hetaryloxy or hetarylthio, to each of which may be fused further saturated or unsaturated 5- to 7-membered rings whose carbon skeleton may be interrupted by one or more —O—, —S—, —NR2—, —N═CR2—, —CO—, —SO— and/or —SO2— moieties, where the entire ring system may be mono- or polysubstituted by the (i), (ii), (iii), (iv) and/or (v) radicals:(i) C1-C30-alkyl whose carbon chain may be interrupted by one or more —O—, —S—, —NR2—, —N═CR2—, —≡C—, —CR2═CR2—, —CO—, —SO— and/or —SO2— moieties and which may be mono- or polysubstituted by: C1-C12-alkoxy, C1-C6-alkylthio, —C≡CR2, —CR2═CR22, hydroxyl, mercapto, halogen, cyano, nitro, —NR7R8, —NR3COR4, —CONR3R4, —SO2NR3R4, —COOR5,—SO3R5, —PR52, —POR5R5, (het)aryl and/or saturated orunsaturated C4-C7-cycloalkyl whose carbon skeleton may be interrupted by one or more —O—, —S—, —NR2—, —N═CR2—, —CR2═CR2—, —CO—, —SO— and/or —SO2— moieties, where the (het)aryl and cycloalkyl radicals may each be mono- or polysubstituted by C1-C18-alkyl and/or the above radicals specified as substituents for alkyl;(ii) C3-C8-cycloalkyl whose carbon skeleton may be interrupted by one or more —O—, —S—, —NR2—, —N═CR2—, —CR2═CR2—, —CO—, —SO— and/or —SO2— moieties and to which may be fused further saturated or unsaturated 5- to 7-membered rings whose carbon skeleton may be interrupted by one or more —O—, —S—, —NR2—, —N═CR2—, —CR2═CR2—, —CO—, —SO— and/or —SO2— moieties, where the entire ring system may be mono- or polysubstituted by: C1-C18-alkyl, C1-C12-alkoxy, C1-C6-alkylthio, —CR2═CR22, hydroxyl, mercapto, halogen, cyano, nitro, —NR7R8, —NR3COR4, —CONR3R4, —SO2NR3R4, —COOR5, —SO3R5, —PR52 and/or —POR5R5; (iii) aryl or hetaryl to which may be fused further saturated or unsaturated 5- to 7-membered rings whose carbon skeleton may be interrupted by one or more —O—, —S—, —NR2—, —N═CR2—, —CR2═CR2—, —CO—, —SO— and/or —SO2— moieties, where the entire ring system may be mono- or polysubstituted by: C1-C18-alkyl, C1-C12-alkoxy, C1-C6-alkylthio, —CR2═CR22, hydroxyl, mercapto, halogen, cyano, nitro, —NR7R8, —NR3COR4, —CONR3R4, —SO2NR3R4, —COOR5, —SO3R5, —PR52, —POR5R5, (het)aryl, (het)aryloxy and/or (het)arylthio, where the (het)aryl radicals may each be mono- or polysubstituted by C1-C18-alkyl, C1-C12-alkoxy, C1-C6-alkylthio, hydroxyl, mercapto, halogen, cyano, nitro, —NR7R8, —NR3COR4, —CONR3R4, —SO2NR3R4, —COOR5, —SO3R5, —PR52, —POR5R5; (iv) a —U-aryl radical which may be mono- or polysubstituted by the above radicals specified as substituents for the aryl radicals (iii), where U is a —O—, —S—, —NR3—, —CO—, —SO— or —SO2— moiety;(v) C1-C12-alkoxy, C1-C6-alkylthio, —C≡CR2, —CR2═CR22, hydroxyl, mercapto, halogen, cyano, nitro, —NR7R8, —NR3COR4, —CONR3R4, —SO2NR3R4, —COOR5, —SO3R5, —PR52 and/or —POR′R5;(vi) E-D-SO3−; D is selected from the group of residues as depicted under (ii) and (iii), whereby the counterion of the anion (—SO3−) respectively cation is selected from the group consisting of metal ion and quarternary ammonium ions L is a chemical bond or an arylene or hetarylene radical, bonded to the rylene skeleton directly or via ethenylene or ethynylene, of the formulae —Ar— —Ar-E-Ar—in which the (het)arylene radicals Ar may be the same or different, may comprise heteroatoms as ring atoms and/or may have fused saturated or unsaturated 5- to 7-membered rings which may likewise comprise heteroatoms, where the entire ring system may be mono- or polysubstituted by phenyl, C1-C12-alkyl, C1-C12-alkoxy, C1-C12-alkylthio and/or —NR3R4; E is a chemical bond or an —O—, —S—, —NR2—, —C≡C—, —CR2═CR2— or C1-C6-alkylene moiety; Z is —O— or —S— or a carbon-carbon single, double or triple bond, provided that L and Z are not simultaneously a chemical bond; R1 is one of the alkyl radicals (i) or (het)aryl radicals (iii) specified as substituents for the R radicals; A is hydrogen;C1-C30-alkyl whose carbon chain may be interrupted by one or more —O—, —S—, —NR2—, —N═CR2—, —C≡C—, —CR2═CR2—, —CO—, —SO— and/or —SO2— moieties and which may be mono- or polysubstituted by the (ii), (iii), (iv) and/or (v) radicals specified as substituents for the R radicals;C3-C8-cycloalkyl to which may be fused further saturated or unsaturated 5- to 7-membered rings whose carbon skeleton may be interrupted by one or more —O—, —S—, —N═CR2—, —N═CR2—, —CR2═CR2—, —CO—, —SO— and/or —SO2— moieties, where the entire ring system may be mono- or polysubstituted by the (i), (ii), (iii), (iv) and/or (v) radicals specified as substituents for the R radicals;aryl or hetaryl to which may be fused further saturated or unsaturated 5- to 7-membered rings whose carbon skeleton may be interrupted by one or more —O—, —S—, —NR2—, —N═CR2—, —CR2═CR2—, —CO—, —SO— and/or —SO2— moieties, where the entire ring system may be mono- or polysubstituted by the (i), (ii), (iii), (iv), (v) radicals specified as substituents for the R radicals, and/or aryl- and/or hetarylazo, each of which may be substituted by C1-C10-alkyl, C1-C6-alkoxy and/or cyano;E-D-SO3−, D is selected from the group of residues as depicted under (ii) and (iii), whereby the counterion of the anion (—SO3−) respectively cation is selected from the group consisting of metal ion and quarternary ammonium ions, R2 is hydrogen or C1-C18-alkyl, where the R2 radicals may be the same or different when they occur more than once; R3, R4 are each independently: hydrogen;C1-C18-alkyl whose carbon chain may be interrupted by one or more —O—, —S—, —CO—, —SO— and/or —SO2— moieties and which may be mono- or polysubstituted by C1-C12-alkoxy, C1-C6-alkylthio, hydroxyl, mercapto, halogen, cyano, nitro and/or —COOR6;aryl or hetaryl to each of which may be fused further saturated or unsaturated 5- to 7-membered rings whose carbon skeleton may be interrupted by one or more —O—, —S—, —CO— and/or —SO2— moieties, where the entire ring system may be mono- or polysubstituted by C1-C12-alkyl and/or the above radicals specified as substituents for alkyl;where the R3 radicals may be the same or different when they occur more than once; R5 is hydrogen, a C1-C18-alkyl whose carbon chain may be interrupted by one or more —O—, —S—, —CO—, —SO— and/or —SO2— moieties and which may be mono- or polysubstituted by C1-C12-alkoxy, C1-C6-alkylthio, hydroxyl, mercapto, halogen, cyano, nitro and/or —COOR6; aryl or hetaryl to each of which may be fused further saturated or unsaturated 5- to 7-membered rings whose carbon skeleton may be interrupted by one or more —O—, —S—, —CO— and/or —SO2— moieties, where the entire ring system may be mono- or polysubstituted by C1-C12-alkyl and/or the above radicals specified as substituents for alkyl, where the R5 radicals may be the same or different when they occur more than once; R6 is C1-C8-alkyl; R7, R8 are each C1-C30-alkyl whose carbon chain may be interrupted by one or more —O—, —S—, —NR2—, —N═CR2—, —C≡C—, —CR2═CR2—, —CO—, —SO— and/or —SO2— moieties and which may be mono- or polysubstituted by: C1-C12-alkoxy, C1-C6-alkylthio, —CR2═CR22, hydroxyl, —NR3R4, —NR3COR4, (het)aryl and/or saturated or unsaturated C4-C7-cycloalkyl whose carbon skeleton may be interrupted by one or more —O—, —S—, —NR2—, —N═CR2— and/or —CR2═CR2 moieties, where the (het)aryl and cycloalkyl radicals may each be mono- or polysubstituted by C1-C18-alkyl and/or the above radicals specified as substituents for alkyl; aryl or hetaryl to which may be fused further saturated or unsaturated 5- to 7-membered rings whose carbon skeleton may be interrupted by one or more —O—, —S—, —NR2—, —N═CR2—, —CR2═CR2—, —CO—, —SO— and/or —SO2— moieties, where the entire ring system may be mono- or polysubstituted by: C1-C18-alkyl, C1-C12-alkoxy, C1-C6-alkylthio, —C≡CR2, —CR2═CR22, hydroxyl, —NR3R4, —NR3COR4, (het)aryl, (het)aryloxy and/or (het)arylthio, where the (het)aryl radicals may in each case be mono- or polysubstituted by C1-C18-alkyl, C1-C12-alkoxy, hydroxyl, —NR3R4 and/or —NR3COR4;joined to the nitrogen atom to form a saturated or unsaturated, 5- to 7-membered ring whose carbon chain may be interrupted by one or more —O—, —S— and/or —NR2— moieties, to which may be fused one or two unsaturated or saturated 4- to 8-membered rings whose carbon chain may likewise be interrupted by these moieties and/or —N═, where the entire ring system may be mono- or polysubstituted by C1-C24-alkyl which may be substituted by C1-C18-alkoxy, C1-C18-alkylthio and/or —NR3R4, (het)aryl which may be mono- or polysubstituted by C1-C18-alkyl and/or the above radicals specified as substituents for alkyl, C1-C18-alkoxy, C1-C18-alkylthio and/or —NR3R4; m is 0; p is 0.
地址 Ludwigshafen DE