CA2569615A1 - Composes de fixation d'acides nucleiques contenant des analogues pyrazolo[3,4-d]pyrimidine de purine 2,6-diamine et leurs utilisations - Google Patents

Composes de fixation d'acides nucleiques contenant des analogues pyrazolo[3,4-d]pyrimidine de purine 2,6-diamine et leurs utilisations Download PDF

Info

Publication number: CA2569615A1
Authority: CA; Canada
Prior art keywords: group; alkyl; nucleic acid; acid binding; substituted
Prior art date: 2000-08-03
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA002569615A

Other languages

English (en)

Inventor

Frank Seela

Frank Bergmann

Herbert Von Der Eltz

Dieter Heindl

Christoph Seidel

Georg Becher

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

F Hoffmann La Roche AG

Original Assignee

Individual

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-08-03

Filing date

2001-07-31

Publication date

2002-02-14

2001-07-31 Application filed by Individual filed Critical Individual

2001-07-31 Priority claimed from CA2416631A external-priority patent/CA2416631C/fr

2002-02-14 Publication of CA2569615A1 publication Critical patent/CA2569615A1/fr

Status Abandoned legal-status Critical Current

Links

102000039446 nucleic acids Human genes 0.000 title claims abstract description 585
108020004707 nucleic acids Proteins 0.000 title claims abstract description 584
150000007523 nucleic acids Chemical class 0.000 title claims abstract description 583
150000001875 compounds Chemical class 0.000 title claims abstract description 479
QUKPALAWEPMWOS-UHFFFAOYSA-N 1h-pyrazolo[3,4-d]pyrimidine Chemical class C1=NC=C2C=NNC2=N1 QUKPALAWEPMWOS-UHFFFAOYSA-N 0.000 title claims description 54
238000000034 method Methods 0.000 claims abstract description 117
ZTAWTRPFJHKMRU-UHFFFAOYSA-N 7-deaza-8-aza-2,6-diaminopurine Chemical class NC1=NC(N)=C2NN=CC2=N1 ZTAWTRPFJHKMRU-UHFFFAOYSA-N 0.000 claims abstract description 46
125000006853 reporter group Chemical group 0.000 claims description 138
125000001424 substituent group Chemical group 0.000 claims description 120
229910052736 halogen Inorganic materials 0.000 claims description 118
-1 OR12 Proteins 0.000 claims description 108
125000000623 heterocyclic group Chemical group 0.000 claims description 108
125000003118 aryl group Chemical group 0.000 claims description 96
125000000217 alkyl group Chemical group 0.000 claims description 82
238000009396 hybridization Methods 0.000 claims description 74
125000006239 protecting group Chemical group 0.000 claims description 71
125000000304 alkynyl group Chemical group 0.000 claims description 67
230000000295 complement effect Effects 0.000 claims description 67
238000003786 synthesis reaction Methods 0.000 claims description 63
230000015572 biosynthetic process Effects 0.000 claims description 61
125000003342 alkenyl group Chemical group 0.000 claims description 60
239000007790 solid phase Substances 0.000 claims description 57
125000004093 cyano group Chemical group *C#N 0.000 claims description 54
239000002773 nucleotide Substances 0.000 claims description 45
125000003729 nucleotide group Chemical group 0.000 claims description 45
229910052757 nitrogen Inorganic materials 0.000 claims description 39
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 37
239000000203 mixture Substances 0.000 claims description 37
238000006243 chemical reaction Methods 0.000 claims description 32
229910052739 hydrogen Inorganic materials 0.000 claims description 30
150000003839 salts Chemical class 0.000 claims description 30
238000002844 melting Methods 0.000 claims description 28
230000008018 melting Effects 0.000 claims description 27
125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 25
150000003254 radicals Chemical class 0.000 claims description 24
229910052760 oxygen Inorganic materials 0.000 claims description 23
239000001257 hydrogen Substances 0.000 claims description 22
235000000346 sugar Nutrition 0.000 claims description 22
229910052717 sulfur Inorganic materials 0.000 claims description 22
229910052740 iodine Inorganic materials 0.000 claims description 21
238000004132 cross linking Methods 0.000 claims description 20
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239000002243 precursor Substances 0.000 claims description 17
238000003752 polymerase chain reaction Methods 0.000 claims description 14
239000000758 substrate Substances 0.000 claims description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 13
239000001226 triphosphate Substances 0.000 claims description 12
235000011178 triphosphate Nutrition 0.000 claims description 12
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230000007062 hydrolysis Effects 0.000 claims description 11
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125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 10
101100212791 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) YBL068W-A gene Proteins 0.000 claims description 10
UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 claims description 10
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125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
239000007850 fluorescent dye Substances 0.000 claims description 8
238000010791 quenching Methods 0.000 claims description 8
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239000011324 bead Substances 0.000 claims description 7
230000003993 interaction Effects 0.000 claims description 7
125000000464 thioxo group Chemical group S=* 0.000 claims description 7
125000002264 triphosphate group Chemical group [H]OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O* 0.000 claims description 7
JJTNLWSCFYERCK-UHFFFAOYSA-N 7h-pyrrolo[2,3-d]pyrimidine Chemical compound N1=CN=C2NC=CC2=C1 JJTNLWSCFYERCK-UHFFFAOYSA-N 0.000 claims description 6
101100294103 Caenorhabditis elegans nhr-31 gene Proteins 0.000 claims description 6
239000011521 glass Substances 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
108060002716 Exonuclease Proteins 0.000 claims description 4
238000010521 absorption reaction Methods 0.000 claims description 4
230000002255 enzymatic effect Effects 0.000 claims description 4
102000013165 exonuclease Human genes 0.000 claims description 4
230000002349 favourable effect Effects 0.000 claims description 4
GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 claims description 4
239000000463 material Substances 0.000 claims description 4
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239000002299 complementary DNA Substances 0.000 claims description 3
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238000005259 measurement Methods 0.000 claims description 3
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239000008194 pharmaceutical composition Substances 0.000 claims description 3
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 3
238000006116 polymerization reaction Methods 0.000 claims description 3
239000000377 silicon dioxide Substances 0.000 claims description 3
125000006323 alkenyl amino group Chemical group 0.000 claims description 2
125000006319 alkynyl amino group Chemical group 0.000 claims description 2
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
230000014509 gene expression Effects 0.000 claims description 2
239000005373 porous glass Substances 0.000 claims description 2
PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 claims description 2
ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 claims description 2
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 50
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 18
125000006375 C2-C10 alkynyl group Chemical group 0.000 claims 8
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
229910019142 PO4 Inorganic materials 0.000 claims 1
230000004075 alteration Effects 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
239000001177 diphosphate Substances 0.000 claims 1
XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims 1
235000011180 diphosphates Nutrition 0.000 claims 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
239000010452 phosphate Substances 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 102
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239000002777 nucleoside Substances 0.000 description 91
239000000523 sample Substances 0.000 description 69
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 60
JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 description 60
125000003835 nucleoside group Chemical group 0.000 description 56
108020004414 DNA Proteins 0.000 description 54
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 46
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KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 28
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MSSXOMSJDRHRMC-UHFFFAOYSA-N 9H-purine-2,6-diamine Chemical compound NC1=NC(N)=C2NC=NC2=N1 MSSXOMSJDRHRMC-UHFFFAOYSA-N 0.000 description 13
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CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 11
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238000010647 peptide synthesis reaction Methods 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
229910000064 phosphane Inorganic materials 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical class [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
125000004437 phosphorous atom Chemical group 0.000 description 1
238000001394 phosphorus-31 nuclear magnetic resonance spectrum Methods 0.000 description 1
230000000865 phosphorylative effect Effects 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920005990 polystyrene resin Polymers 0.000 description 1
230000008092 positive effect Effects 0.000 description 1
230000000063 preceeding effect Effects 0.000 description 1
230000008569 process Effects 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 1
150000003194 psoralenes Chemical class 0.000 description 1
IGFXRKMLLMBKSA-UHFFFAOYSA-N purine Chemical compound N1=C[N]C2=NC=NC2=C1 IGFXRKMLLMBKSA-UHFFFAOYSA-N 0.000 description 1
239000002213 purine nucleotide Substances 0.000 description 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
150000004943 pyrrolo[2,3-d]pyrimidines Chemical class 0.000 description 1
238000011002 quantification Methods 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
230000008439 repair process Effects 0.000 description 1
239000002342 ribonucleoside Substances 0.000 description 1
239000002336 ribonucleotide Substances 0.000 description 1
125000002652 ribonucleotide group Chemical class 0.000 description 1
108091092562 ribozyme Proteins 0.000 description 1
TZSZZENYCISATO-WIOPSUGQSA-N rodatristat Chemical compound CCOC(=O)[C@@H]1CC2(CN1)CCN(CC2)c1cc(O[C@H](c2ccc(Cl)cc2-c2ccccc2)C(F)(F)F)nc(N)n1 TZSZZENYCISATO-WIOPSUGQSA-N 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
238000004574 scanning tunneling microscopy Methods 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
229910052814 silicon oxide Inorganic materials 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
210000003802 sputum Anatomy 0.000 description 1
208000024794 sputum Diseases 0.000 description 1
229910052682 stishovite Inorganic materials 0.000 description 1
238000005728 strengthening Methods 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
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239000000725 suspension Substances 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
238000012360 testing method Methods 0.000 description 1
BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
230000036962 time dependent Effects 0.000 description 1
238000012546 transfer Methods 0.000 description 1
230000007704 transition Effects 0.000 description 1
238000013519 translation Methods 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
229910052905 tridymite Inorganic materials 0.000 description 1
150000005691 triesters Chemical class 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
238000012800 visualization Methods 0.000 description 1
102000035029 vitamin receptors Human genes 0.000 description 1
108091005463 vitamin receptors Proteins 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Landscapes

Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA002569615A 2000-08-03 2001-07-31 Composes de fixation d'acides nucleiques contenant des analogues pyrazolo[3,4-d]pyrimidine de purine 2,6-diamine et leurs utilisations Abandoned CA2569615A1 (fr)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
EP00116816.0		2000-08-03
EP00116816		2000-08-03
EP01109438		2001-04-24
EP01109438.0		2001-04-24
CA2416631A CA2416631C (fr)	2000-08-03	2001-07-31	Composes de fixation d'acides nucleiques contenant des analogues pyrazolo[3,4-d]pyrimidine de purine 2,6-diamine et leurs utilisations

Related Parent Applications (1)

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CA2416631A Division CA2416631C (fr)	2000-08-03	2001-07-31	Composes de fixation d'acides nucleiques contenant des analogues pyrazolo[3,4-d]pyrimidine de purine 2,6-diamine et leurs utilisations

Publications (1)

Publication Number	Publication Date
CA2569615A1 true CA2569615A1 (fr)	2002-02-14

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CA002569615A Abandoned CA2569615A1 (fr)	2000-08-03	2001-07-31	Composes de fixation d'acides nucleiques contenant des analogues pyrazolo[3,4-d]pyrimidine de purine 2,6-diamine et leurs utilisations

Country Status (1)

Country	Link
CA (1)	CA2569615A1 (fr)

2001
- 2001-07-31 CA CA002569615A patent/CA2569615A1/fr not_active Abandoned

Legal Events

Date	Code	Title	Description
2006-12-18	EEER	Examination request
2010-08-02	FZDE	Dead

Publication	Publication Date	Title
CA2416631C (fr)	2011-11-22	Composes de fixation d'acides nucleiques contenant des analogues pyrazolo[3,4-d]pyrimidine de purine 2,6-diamine et leurs utilisations
JP5231032B2 (ja)	2013-07-10	オリゴヌクレオチド・ハイブリダイゼーションにユニバーサル・ヌクレオシドとして使用されるｎ８−及びｃ８−連結プリン塩基、並びに構造的に関連したヘテロ環
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US7612187B2 (en)	2009-11-03	2-azapurine compounds and their uses
US20080038745A1 (en)	2008-02-14	Nucleotide analogs with six-membered rings
Seela et al.	1999	The base‐pairing properties of 7‐deaza‐2′‐deoxyisoguanosine and 2′‐deoxyisoguanosine in oligonucleotide duplexes with parallel and antiparallel chain orientation
CA2215489A1 (fr)	1998-03-13	Procede d'amplification des acides nucleiques
Becher et al.	2001	Major‐Groove‐Halogenated DNA: The Effects of Bromo and Iodo Substituents Replacing H− C (7) of 8‐Aza‐7‐deazapurine‐2, 6‐diamine or H− C (5) of Uracil Residues
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CA2569615A1 (fr)	2002-02-14	Composes de fixation d'acides nucleiques contenant des analogues pyrazolo[3,4-d]pyrimidine de purine 2,6-diamine et leurs utilisations
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