Purine analog nucleoside and nucleotide compounds
First Claim
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1. Nucleoside derivatives of formula I ##STR6## wherein Ba is an indolyl (A), benzimidazolyl (B), pyrrolopyridinyl (C), imidazopyridinyl (D), triazolopyrimidinyl (E), imidazotriazinyl (F) or imidazopyrimidinyl (G) group, of the following formulae, respectively:
- ##STR7## wherein R1, R2, R3, which can be the same or different, are hydrogen, halogen, C1 -C7 -alkyl, C2 -C7 -alkenyl, hydroxy, mercapto, C1 -C7 -alkylthio, C1 -C7 -alkoxy, C2 -C7 -alkenyloxy, aryl-C1 -C5 -alkyl, aryl-C2 -C5 -alkenyl, aryl-C1 -C5 -alkoxy, aryl-C2 -C5 -alkenyloxy, aryloxy, nitro, amino-C1 -C7 -alkyl, C1 -C7 -alkylamino-C1 -C7 -alkyl, di-C1 -C7 -alkylamino-C1 -C7 -alkyl, amino, substituted amino group of the formula --NHR4 or --N(R4)2 or an imino group --N═
CH--R4, wherein R4 is C1 -C7 -alkyl, C2 -C7 -alkenyl, C3 -C7 -cycloalkyl, C3 -C7 -cycloalkyl-C1 -C7 -alkyl, C3 -C7 -cycloalkenyl, C1 -C7 -alkoxy-C1 -C7 -alkyl, halogen-C1 -C7 -alkyl, hydroxy-C1 -C7 -alkyl, aryl-C.sub. 1 -C5 -alkyl, aryl-C2 -C5 -alkenyl, hetaryl-C1 -C5 -alkyl or hetaryl-C2 -C5 -alkenyl radical, wherein the aryl and hetaryl moieties are unsubstituted or are substituted one, two or three times by C1 -C6 -alkyl, C2 -C6 -alkenyl, C1 -C6 -alkoxy, halogen or hydroxyl, or R4 is amino-C1 -C7 -alkyl, C1 -C7 -alkylamino-C1 -C7 -alkyl or di-C1 -C7 -alkylamino-C1 -C7 -alkyl and, in the case of the --NHR4 and --N═
CH--R4 groups, R4 can additionally be amino, C1 -C7 -alkylamino, di-C1 -C7 -alkylamino or C1 -C7 -alkoxy or, in the case of the --N(R4)2 group, the two nitrogen substituents R4 together can form a C1 -C7 -alkylidene group which, in turn, can be unsubstituted or substituted by C1 -C7 -alkoxy, C1 -C7 -alkylamino or di-C1 -C7 -alkylamino, wherein said aryl is phenyl or naphthyl and said hetaryl is furanyl, thienyl or pyridyl, R5, R6, R7, and R8 each are hydrogen, or one or two of R5, R6, R7, and R8 are hydroxyl, halogen, cyano, azido or a substituted amino group --NHR4 or --N(R4)2, or and R5 and R7 can together represent a further bond between C-2'"'"' and C-3'"'"', and Y is hydrogen or C1 -C7 -alkylcarbonyl, monophosphate, diphosphate or triphosphate,with the provisos thata) when R6 is a hydroxyl group, R8 is other than a hydrogen atom or a hydroxyl group,b) when Ba is the group (B) , R6 is other than a halogen, amino or azido group,c) when Ba is the group (D) and R2 is hydrogen, R1 is other than chlorine or amino and R6 is other than hydrogen or chlorine, andd) When Ba is the group (E) and R1 is amino, R5 and R7 cannot together represent a bond,as well as their possible α and
β
-anomers, , N7 -, N8 - or N9 regioisomers (purine nomenclature), tautomers and salts, and nucleic acids which contain compounds of the formula I as constructional units.
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Abstract
The invention concerns nucleoside derivatives of the formula I ##STR1## in which Ba signifies an indolyl (A), benzimidazolyl (B), pyrrolopyridinyl (C), imidazopyridinyl (D), triazolopyrimidinyl (E), imidazotriazinyl (F) or imidazopyrimidinyl (G) group substituted by R1, R2 and R3, in which R1, R2 and R3, which can be the same or different, signify hydrogen, halogen, a C1 -C7 -alkyl, C2 -C7 -alkenyl, hydroxy, mercapto, C1 -C7 -alkylthio, C1 -C7 -alkoxy, C2 -C7 -alkenyloxy, ar-C1 -C5 -alkyl, ar-C2 -C5 -alkenyl, ar-C1 -C5 -alkoxy, ar-C2 -C5 -alkenyloxy, aryloxy, nitro, amino-C1 -C7 -alkyl, C1 -C7 -alkylamino-C1 -C7 -alkyl, di-C1 -C7 -alkylamino-C1 -C7 -alkyl, amino, a substituted amino group --NMR4 or --N(R4)2 or an imino group --N═CH--R4, and R4 has the meaning given in the description, R5, R6, R7 and R8 each signify hydrogen or one or two of the radicals R5, R6, R7 and R8 a hydroxyl, halogen, cyano, azido or a substituted amino group --NHR4 or --N(R4)2 or R5 and R7 can together represent a further bond between C-2'"'"' and C-3'"'"' and Y represents hydrogen or a C1 -C7 -alkylcarbonyl, monophosphate, diphosphate or triphosphate group, whereby "aryl" signifies a phenyl or naphthyl group and "hetaryl" a furanyl, thienyl or pyridyl group, as well as their possible anomers, N7 - or N9 -regioisomers (purine nomenclature), tautomers and salts.
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Citations
12 Claims
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1. Nucleoside derivatives of formula I ##STR6## wherein Ba is an indolyl (A), benzimidazolyl (B), pyrrolopyridinyl (C), imidazopyridinyl (D), triazolopyrimidinyl (E), imidazotriazinyl (F) or imidazopyrimidinyl (G) group, of the following formulae, respectively:
- ##STR7## wherein R1, R2, R3, which can be the same or different, are hydrogen, halogen, C1 -C7 -alkyl, C2 -C7 -alkenyl, hydroxy, mercapto, C1 -C7 -alkylthio, C1 -C7 -alkoxy, C2 -C7 -alkenyloxy, aryl-C1 -C5 -alkyl, aryl-C2 -C5 -alkenyl, aryl-C1 -C5 -alkoxy, aryl-C2 -C5 -alkenyloxy, aryloxy, nitro, amino-C1 -C7 -alkyl, C1 -C7 -alkylamino-C1 -C7 -alkyl, di-C1 -C7 -alkylamino-C1 -C7 -alkyl, amino, substituted amino group of the formula --NHR4 or --N(R4)2 or an imino group --N═
CH--R4, wherein R4 is C1 -C7 -alkyl, C2 -C7 -alkenyl, C3 -C7 -cycloalkyl, C3 -C7 -cycloalkyl-C1 -C7 -alkyl, C3 -C7 -cycloalkenyl, C1 -C7 -alkoxy-C1 -C7 -alkyl, halogen-C1 -C7 -alkyl, hydroxy-C1 -C7 -alkyl, aryl-C.sub. 1 -C5 -alkyl, aryl-C2 -C5 -alkenyl, hetaryl-C1 -C5 -alkyl or hetaryl-C2 -C5 -alkenyl radical, wherein the aryl and hetaryl moieties are unsubstituted or are substituted one, two or three times by C1 -C6 -alkyl, C2 -C6 -alkenyl, C1 -C6 -alkoxy, halogen or hydroxyl, or R4 is amino-C1 -C7 -alkyl, C1 -C7 -alkylamino-C1 -C7 -alkyl or di-C1 -C7 -alkylamino-C1 -C7 -alkyl and, in the case of the --NHR4 and --N═
CH--R4 groups, R4 can additionally be amino, C1 -C7 -alkylamino, di-C1 -C7 -alkylamino or C1 -C7 -alkoxy or, in the case of the --N(R4)2 group, the two nitrogen substituents R4 together can form a C1 -C7 -alkylidene group which, in turn, can be unsubstituted or substituted by C1 -C7 -alkoxy, C1 -C7 -alkylamino or di-C1 -C7 -alkylamino, wherein said aryl is phenyl or naphthyl and said hetaryl is furanyl, thienyl or pyridyl, R5, R6, R7, and R8 each are hydrogen, or one or two of R5, R6, R7, and R8 are hydroxyl, halogen, cyano, azido or a substituted amino group --NHR4 or --N(R4)2, or and R5 and R7 can together represent a further bond between C-2'"'"' and C-3'"'"', and Y is hydrogen or C1 -C7 -alkylcarbonyl, monophosphate, diphosphate or triphosphate,with the provisos that a) when R6 is a hydroxyl group, R8 is other than a hydrogen atom or a hydroxyl group, b) when Ba is the group (B) , R6 is other than a halogen, amino or azido group, c) when Ba is the group (D) and R2 is hydrogen, R1 is other than chlorine or amino and R6 is other than hydrogen or chlorine, and d) When Ba is the group (E) and R1 is amino, R5 and R7 cannot together represent a bond, as well as their possible α and
β
-anomers, , N7 -, N8 - or N9 regioisomers (purine nomenclature), tautomers and salts, and nucleic acids which contain compounds of the formula I as constructional units. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11)
- ##STR7## wherein R1, R2, R3, which can be the same or different, are hydrogen, halogen, C1 -C7 -alkyl, C2 -C7 -alkenyl, hydroxy, mercapto, C1 -C7 -alkylthio, C1 -C7 -alkoxy, C2 -C7 -alkenyloxy, aryl-C1 -C5 -alkyl, aryl-C2 -C5 -alkenyl, aryl-C1 -C5 -alkoxy, aryl-C2 -C5 -alkenyloxy, aryloxy, nitro, amino-C1 -C7 -alkyl, C1 -C7 -alkylamino-C1 -C7 -alkyl, di-C1 -C7 -alkylamino-C1 -C7 -alkyl, amino, substituted amino group of the formula --NHR4 or --N(R4)2 or an imino group --N═
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12. Nucleoside derivative of formula I ##STR8## wherein Ba is an indolyl, pyrrolopyridinyl, imidazopyridinyl, imidazotriazinyl or imidazopyrimidinyl group;
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R1 is hydrogen, amino, C1-C6-alkoxy, halogen or nitro; R2 is hydrogen, halogen or amino; R3 is hydrogen; R5 is hydrogen; R6 is hydrogen, halogen, cyano or azido; R7 is hydrogen; and R8 is hydrogen or R5 and R7 together form a bond; with the proviso that when Ba is the group (E) and R1 is amino, R5 and R7 cannot together represent a bond, as well as their possible α and
β
-anomers, N7 -, N8 - or N9 regioisomers (purine nomenclature), tautomers and salts, and nucleic acids which contain compounds of the formula I as constructional units.
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Specification
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Current AssigneeBoehringer Mannheim GmbH (Roche Holding AG)
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Original AssigneeBoehringer Mannheim GmbH (Roche Holding AG)
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InventorsRoling, Angelika, Bourgeouis, Werner, Koch, Edith, Seela, Frank, Rosemeyer, Helmut, Mertens, Alfred, Konig, Bernhard, Zilch, Harald, Gumbiowski, Rainer
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Primary Examiner(s)Robinson, Douglas W.
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Assistant Examiner(s)Wilson, James O.
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Application NumberUS07/809,506Time in Patent Office1,285 DaysField of Search536/26.7, 536/26.71, 536/26.74, 536/27.11, 536/27.13, 536/27.2, 536/27.21, 536/27.23, 536/27.6, 536/27.61, 536/27.62, 536/27.63, 536/27.7 , 536/27.8, 536/27.81, 514/45, 514/46, 514/47, 514/48US Class Current536/26.7CPC Class CodesA61P 31/12 AntiviralsC07H 19/04 Heterocyclic radicals conta...
