IL173723A - Transformed xanthine-8-troarili, pharmaceutical preparations containing them and their use in the preparation of medicines - Google Patents

Info

Publication number

IL173723A

IL173723A IL173723A IL17372306A IL173723A IL 173723 A IL173723 A IL 173723A IL 173723 A IL173723 A IL 173723A IL 17372306 A IL17372306 A IL 17372306A IL 173723 A IL173723 A IL 173723A

Authority

IL

Israel

Prior art keywords

alkyl

compound

aryl

pyridyl

xanthine

Prior art date

2003-08-25

Links

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• Global Dossier
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• 239000003814 drug Substances 0.000 title claims description 11
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 10
• 238000004519 manufacturing process Methods 0.000 title claims description 8
• 229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 title description 2
• LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims description 459
• 229940075420 xanthine Drugs 0.000 claims description 232
• 125000000217 alkyl group Chemical group 0.000 claims description 212
• 150000001875 compounds Chemical class 0.000 claims description 202
• -1 R^^CCi-Cgialkyl Chemical group 0.000 claims description 174
• 125000003118 aryl group Chemical group 0.000 claims description 107
• 125000005843 halogen group Chemical group 0.000 claims description 91
• 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 56
• 125000001072 heteroaryl group Chemical group 0.000 claims description 55
• 125000000623 heterocyclic group Chemical group 0.000 claims description 55
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 54
• 125000001424 substituent group Chemical group 0.000 claims description 41
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 38
• 150000002431 hydrogen Chemical class 0.000 claims description 38
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 38
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 37
• 125000005913 (C3-C6) cycloalkyl 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 34
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 33
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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 29
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 28
• 125000003342 alkenyl group Chemical group 0.000 claims description 27
• 125000000304 alkynyl group Chemical group 0.000 claims description 27
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 25
• 150000003839 salts Chemical class 0.000 claims description 25
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 24
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
• 239000000203 mixture Substances 0.000 claims description 22
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 20
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 18
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 17
• 150000001412 amines Chemical class 0.000 claims description 17
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 15
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 15
• 125000006413 ring segment Chemical group 0.000 claims description 15
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 14
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
• 101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 claims description 12
• 241000124008 Mammalia Species 0.000 claims description 12
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 12
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 12
• 125000003545 alkoxy group Chemical group 0.000 claims description 11
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
• 229910052757 nitrogen Inorganic materials 0.000 claims description 11
• 125000004076 pyridyl group Chemical group 0.000 claims description 11
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 11
• 125000002785 azepinyl group Chemical group 0.000 claims description 10
• 125000002757 morpholinyl group Chemical group 0.000 claims description 10
• 125000005936 piperidyl group Chemical group 0.000 claims description 10
• 208000006673 asthma Diseases 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
• 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
• 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 claims description 8
• 125000005842 heteroatom 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
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 8
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 7
• 206010022489 Insulin Resistance Diseases 0.000 claims description 7
• 125000004429 atom Chemical group 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
• 229920006395 saturated elastomer Polymers 0.000 claims description 7
• 125000001544 thienyl group Chemical group 0.000 claims description 7
• 125000001246 bromo group Chemical group Br* 0.000 claims description 6
• 125000005592 polycycloalkyl group Polymers 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• 229910003827 NRaRb Inorganic materials 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
• 229910052740 iodine Inorganic materials 0.000 claims description 4
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 3
• 125000004414 alkyl thio group Chemical group 0.000 claims description 3
• 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 10
• KQUAXDUORCKXRU-UHFFFAOYSA-N 1-cyclopropyl-3-ethyl-8-[6-(methylamino)pyridin-3-yl]-7h-purine-2,6-dione Chemical compound O=C1N(CC)C=2N=C(C=3C=NC(NC)=CC=3)NC=2C(=O)N1C1CC1 KQUAXDUORCKXRU-UHFFFAOYSA-N 0.000 claims 1
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 183
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
• 238000005160 1H NMR spectroscopy Methods 0.000 description 34
• 210000004027 cell Anatomy 0.000 description 22
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 21
• 238000005481 NMR spectroscopy Methods 0.000 description 20
• 101150078577 Adora2b gene Proteins 0.000 description 18
• 238000000034 method Methods 0.000 description 17
• 230000000694 effects Effects 0.000 description 14
• 108050000203 Adenosine receptors Proteins 0.000 description 13
• 102000009346 Adenosine receptors Human genes 0.000 description 13
• 238000002360 preparation method Methods 0.000 description 13
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• 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 description 12
• 239000007788 liquid Substances 0.000 description 11
• 239000002904 solvent Substances 0.000 description 10
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
• 239000000872 buffer Substances 0.000 description 9
• 238000006243 chemical reaction Methods 0.000 description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
• 239000007787 solid Substances 0.000 description 9
• 239000000243 solution Substances 0.000 description 9
• ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 8
• 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
• 239000005557 antagonist Substances 0.000 description 7
• 230000027455 binding Effects 0.000 description 7
• 230000015572 biosynthetic process Effects 0.000 description 7
• 239000002552 dosage form Substances 0.000 description 7
• 239000012528 membrane Substances 0.000 description 7
• 238000012360 testing method Methods 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
• 239000002126 C01EB10 - Adenosine Substances 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
• 239000004480 active ingredient Substances 0.000 description 6
• 229960005305 adenosine Drugs 0.000 description 6
• 201000010099 disease Diseases 0.000 description 6
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
• 230000014399 negative regulation of angiogenesis Effects 0.000 description 6
• 208000024891 symptom Diseases 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
• 239000002253 acid Substances 0.000 description 5
• 125000002883 imidazolyl group Chemical group 0.000 description 5
• 238000011534 incubation Methods 0.000 description 5
• 125000006178 methyl benzyl group Chemical group 0.000 description 5
• 231100000252 nontoxic Toxicity 0.000 description 5
• 230000003000 nontoxic effect Effects 0.000 description 5
• 150000003254 radicals Chemical class 0.000 description 5
• 239000002287 radioligand Substances 0.000 description 5
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• 206010012689 Diabetic retinopathy Diseases 0.000 description 4
• 206010012735 Diarrhoea Diseases 0.000 description 4
• TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
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• 229940125890 compound Ia Drugs 0.000 description 4
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• 229940079593 drug Drugs 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
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• 125000003373 pyrazinyl group Chemical group 0.000 description 4
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• 101710169336 5'-deoxyadenosine deaminase Proteins 0.000 description 3
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