JP4769721B2 - 置換８−ヘテロアリールキサンチン - Google Patents

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Publication number

JP4769721B2

JP4769721B2 JP2006524755A JP2006524755A JP4769721B2 JP 4769721 B2 JP4769721 B2 JP 4769721B2 JP 2006524755 A JP2006524755 A JP 2006524755A JP 2006524755 A JP2006524755 A JP 2006524755A JP 4769721 B2 JP4769721 B2 JP 4769721B2

Authority

JP

Japan

Prior art keywords

alkyl

aryl

compound

pyridyl

xanthine

Prior art date

2003-08-25

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.)

Expired - Lifetime

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• 150000001875 compounds Chemical class 0.000 claims description 194
• LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims description 193
• -1 pyrrolidyl Chemical group 0.000 claims description 184
• 229940075420 xanthine Drugs 0.000 claims description 100
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 98
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 86
• 239000001257 hydrogen Substances 0.000 claims description 84
• 229910052739 hydrogen Inorganic materials 0.000 claims description 84
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 57
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 54
• 125000005843 halogen group Chemical group 0.000 claims description 48
• 125000000623 heterocyclic group Chemical group 0.000 claims description 42
• 125000001072 heteroaryl group Chemical group 0.000 claims description 41
• 125000001424 substituent group Chemical group 0.000 claims description 41
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 40
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 38
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 38
• 150000002431 hydrogen Chemical group 0.000 claims description 37
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 35
• 125000000217 alkyl group Chemical group 0.000 claims description 34
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 32
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 30
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 29
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 28
• 125000003342 alkenyl group Chemical group 0.000 claims description 26
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 25
• 125000000304 alkynyl group Chemical group 0.000 claims description 25
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 24
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 24
• 125000003118 aryl group Chemical group 0.000 claims description 23
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
• 150000003839 salts Chemical class 0.000 claims description 19
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 17
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 17
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
• OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims description 16
• 150000001412 amines Chemical class 0.000 claims description 15
• 230000000694 effects Effects 0.000 claims description 14
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 14
• 241000124008 Mammalia Species 0.000 claims description 13
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
• 125000006413 ring segment Chemical group 0.000 claims description 13
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 13
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 13
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
• 201000010099 disease Diseases 0.000 claims description 12
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
• 229910052757 nitrogen Inorganic materials 0.000 claims description 12
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• 125000005936 piperidyl group Chemical group 0.000 claims description 12
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 12
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 11
• 125000002785 azepinyl group Chemical group 0.000 claims description 10
• 239000003814 drug Substances 0.000 claims description 10
• 125000002757 morpholinyl group Chemical group 0.000 claims description 10
• 125000003545 alkoxy group Chemical group 0.000 claims description 9
• 125000004429 atom Chemical group 0.000 claims description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
• 125000004076 pyridyl group Chemical group 0.000 claims description 9
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 8
• 239000002126 C01EB10 - Adenosine Substances 0.000 claims description 8
• 229960005305 adenosine Drugs 0.000 claims description 8
• 208000006673 asthma Diseases 0.000 claims description 8
• 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 8
• 125000002950 monocyclic group Chemical group 0.000 claims description 8
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 8
• 125000004193 piperazinyl group Chemical group 0.000 claims description 8
• 208000024891 symptom Diseases 0.000 claims description 8
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 8
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 7
• 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 7
• 125000005842 heteroatom Chemical group 0.000 claims description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
• 125000006178 methyl benzyl group Chemical group 0.000 claims description 7
• 125000001544 thienyl group Chemical group 0.000 claims description 7
• 206010022489 Insulin Resistance Diseases 0.000 claims description 6
• 125000001246 bromo group Chemical group Br* 0.000 claims description 6
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 125000005592 polycycloalkyl group Polymers 0.000 claims description 6
• 229920006395 saturated elastomer Polymers 0.000 claims description 6
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 5
• 206010012735 Diarrhoea Diseases 0.000 claims description 5
• 208000017442 Retinal disease Diseases 0.000 claims description 5
• 206010038923 Retinopathy Diseases 0.000 claims description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
• 125000002619 bicyclic group Chemical group 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• 206010012601 diabetes mellitus Diseases 0.000 claims description 5
• 239000001301 oxygen Substances 0.000 claims description 5
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 5
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 4
• 206010063837 Reperfusion injury Diseases 0.000 claims description 4
• 208000026935 allergic disease Diseases 0.000 claims description 4
• 230000008485 antagonism Effects 0.000 claims description 4
• 208000028867 ischemia Diseases 0.000 claims description 4
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
• 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 claims description 3
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 208000023275 Autoimmune disease Diseases 0.000 claims description 3
• 206010020751 Hypersensitivity Diseases 0.000 claims description 3
• 230000009471 action Effects 0.000 claims description 3
• 230000007815 allergy Effects 0.000 claims description 3
• 206010028980 Neoplasm Diseases 0.000 claims description 2
• 201000011510 cancer Diseases 0.000 claims description 2
• 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 183
• 238000005481 NMR spectroscopy Methods 0.000 description 58
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
• 102000009346 Adenosine receptors Human genes 0.000 description 24
• 108050000203 Adenosine receptors Proteins 0.000 description 24
• 210000004027 cell Anatomy 0.000 description 22
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 21
• 239000000203 mixture Substances 0.000 description 21
• 102000005962 receptors Human genes 0.000 description 16
• 108020003175 receptors Proteins 0.000 description 16
• 238000012360 testing method Methods 0.000 description 16
• 238000000034 method Methods 0.000 description 15
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• 239000007788 liquid Substances 0.000 description 11
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 10
• 238000002360 preparation method Methods 0.000 description 10
• 239000002904 solvent Substances 0.000 description 10
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
• 0 Cc1nccc(*)c1 Chemical compound Cc1nccc(*)c1 0.000 description 8
• 230000015572 biosynthetic process Effects 0.000 description 8
• 239000000872 buffer Substances 0.000 description 8
• 239000007787 solid Substances 0.000 description 8
• 239000000243 solution Substances 0.000 description 8
• ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 8
• DFKVQPMXXSMIRH-UHFFFAOYSA-N 1,3-diethyl-8-(6-hydrazinylpyridin-3-yl)-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CC)C(=O)N(CC)C=2N=C1C1=CC=C(NN)N=C1 DFKVQPMXXSMIRH-UHFFFAOYSA-N 0.000 description 7
• LFXCYVITBNVTHL-UHFFFAOYSA-N 8-(6-chloropyridin-3-yl)-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C1=CC=C(Cl)N=C1 LFXCYVITBNVTHL-UHFFFAOYSA-N 0.000 description 7
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 7
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
• 239000004480 active ingredient Substances 0.000 description 7
• 230000027455 binding Effects 0.000 description 7
• 239000002552 dosage form Substances 0.000 description 7
• 239000012528 membrane Substances 0.000 description 7
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 6
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 6
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
• 239000007995 HEPES buffer Substances 0.000 description 6
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
• 239000005557 antagonist Substances 0.000 description 6
• 238000006243 chemical reaction Methods 0.000 description 6
• 238000001816 cooling Methods 0.000 description 6
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 6
• 238000011534 incubation Methods 0.000 description 6
• 238000003786 synthesis reaction Methods 0.000 description 6
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 5
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
• 239000002775 capsule Substances 0.000 description 5
• 229940125890 compound Ia Drugs 0.000 description 5
• 229940079593 drug Drugs 0.000 description 5
• 238000007429 general method Methods 0.000 description 5
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• 230000003000 nontoxic effect Effects 0.000 description 5
• 239000003826 tablet Substances 0.000 description 5
• 101710169336 5'-deoxyadenosine deaminase Proteins 0.000 description 4
• 102000055025 Adenosine deaminases Human genes 0.000 description 4
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
• 239000006185 dispersion Substances 0.000 description 4
• BRZYSWJRSDMWLG-CAXSIQPQSA-N geneticin Natural products O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](C(C)O)O2)N)[C@@H](N)C[C@H]1N BRZYSWJRSDMWLG-CAXSIQPQSA-N 0.000 description 4
• 125000002883 imidazolyl group Chemical group 0.000 description 4
• 125000001041 indolyl group Chemical group 0.000 description 4
• 238000002347 injection Methods 0.000 description 4
• 239000007924 injection Substances 0.000 description 4
• 125000005956 isoquinolyl group Chemical group 0.000 description 4
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
• 230000014399 negative regulation of angiogenesis Effects 0.000 description 4
• 239000000843 powder Substances 0.000 description 4
• 238000012746 preparative thin layer chromatography Methods 0.000 description 4
• 238000000159 protein binding assay Methods 0.000 description 4
• 239000000296 purinergic P1 receptor antagonist Substances 0.000 description 4
• 125000003373 pyrazinyl group Chemical group 0.000 description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 description 4
• 125000000168 pyrrolyl group Chemical group 0.000 description 4
• 125000005493 quinolyl group Chemical group 0.000 description 4
• 239000002287 radioligand Substances 0.000 description 4
• 125000003831 tetrazolyl group Chemical group 0.000 description 4
• 229960000278 theophylline Drugs 0.000 description 4
• 238000002560 therapeutic procedure Methods 0.000 description 4
• 125000000335 thiazolyl group Chemical group 0.000 description 4
• 125000004306 triazinyl group Chemical group 0.000 description 4
• 125000001425 triazolyl group Chemical group 0.000 description 4
• FMEBIWNKYZUWFV-UHFFFAOYSA-N 6-chloropyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)N=C1 FMEBIWNKYZUWFV-UHFFFAOYSA-N 0.000 description 3
• BLHCMGRVFXRYRN-UHFFFAOYSA-N 6-hydroxynicotinic acid Chemical compound OC(=O)C1=CC=C(O)N=C1 BLHCMGRVFXRYRN-UHFFFAOYSA-N 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
• FFBDFADSZUINTG-UHFFFAOYSA-N DPCPX Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C1CCCC1 FFBDFADSZUINTG-UHFFFAOYSA-N 0.000 description 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
• 108010010803 Gelatin Proteins 0.000 description 3
• 239000012981 Hank's balanced salt solution Substances 0.000 description 3
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
• JADDQZYHOWSFJD-FLNNQWSLSA-N N-ethyl-5'-carboxamidoadenosine Chemical compound O[C@@H]1[C@H](O)[C@@H](C(=O)NCC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 JADDQZYHOWSFJD-FLNNQWSLSA-N 0.000 description 3
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
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• LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 3
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• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
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• RIRGCFBBHQEQQH-SSFGXONLSA-N (-)-n6-(2-phenylisopropyl)adenosine Chemical compound C([C@@H](C)NC=1C=2N=CN(C=2N=CN=1)[C@H]1[C@@H]([C@H](O)[C@@H](CO)O1)O)C1=CC=CC=C1 RIRGCFBBHQEQQH-SSFGXONLSA-N 0.000 description 2
• KYOSRONGDTVPDJ-NVQRDWNXSA-N (2r,3r,4s,5r)-2-(6-anilinopurin-9-yl)-5-(hydroxymethyl)-2-propan-2-yloxolane-3,4-diol Chemical compound C1=NC2=C(NC=3C=CC=CC=3)N=CN=C2N1[C@]1(C(C)C)O[C@H](CO)[C@@H](O)[C@H]1O KYOSRONGDTVPDJ-NVQRDWNXSA-N 0.000 description 2
• 125000004233 1,3-benzodiazepinyl group Chemical group N1C(=NC=CC2=C1C=CC=C2)* 0.000 description 2
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