HRP20000894A2 - 2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives - Google Patents
2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives Download PDFInfo
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- HRP20000894A2 HRP20000894A2 HR20000894A HRP20000894A HRP20000894A2 HR P20000894 A2 HRP20000894 A2 HR P20000894A2 HR 20000894 A HR20000894 A HR 20000894A HR P20000894 A HRP20000894 A HR P20000894A HR P20000894 A2 HRP20000894 A2 HR P20000894A2
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- compound represented
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- ethylamino
- alkyl
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- YQUJSBYIKMQCIT-UHFFFAOYSA-N 2-purin-9-yloxolane-3,4-diol Chemical class OC1C(O)COC1N1C2=NC=NC=C2N=C1 YQUJSBYIKMQCIT-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 169
- 238000006243 chemical reaction Methods 0.000 claims description 35
- -1 cyclopropenylmethyl Chemical group 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 238000011282 treatment Methods 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 230000008569 process Effects 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 239000012453 solvate Substances 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 12
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
- 238000010511 deprotection reaction Methods 0.000 claims description 6
- 229910005965 SO 2 Inorganic materials 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 125000002785 azepinyl group Chemical group 0.000 claims description 4
- 125000002393 azetidinyl group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical group C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 3
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 3
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 claims description 2
- 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 2
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 2
- 238000011321 prophylaxis Methods 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 125000004545 purin-9-yl group Chemical group N1=CN=C2N(C=NC2=C1)* 0.000 claims 2
- XIPRRYPDZCQSJK-CKXMCULTSA-N (2r,3r,4s,5r)-2-[6-(2,2-diphenylethylamino)-2-(2-piperidin-1-ylethylamino)purin-9-yl]-5-[2-(2-hydroxyethyl)tetrazol-5-yl]oxolane-3,4-diol Chemical compound OCCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCN4CCCCC4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 XIPRRYPDZCQSJK-CKXMCULTSA-N 0.000 claims 1
- NQDWZMYMLQGIIM-KCIBBDPESA-N (2r,3r,4s,5r)-2-[6-(2,2-diphenylethylamino)-2-(2-piperidin-1-ylethylamino)purin-9-yl]-5-[2-(3-hydroxypropyl)tetrazol-5-yl]oxolane-3,4-diol Chemical compound OCCCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCN4CCCCC4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 NQDWZMYMLQGIIM-KCIBBDPESA-N 0.000 claims 1
- VSPPBGVEBYWNIY-CTMYTVLESA-N (2r,3s,4r,5r)-2-(2-cyclobutyltetrazol-5-yl)-5-[6-(2,2-diphenylethylamino)-2-(2-piperidin-1-ylethylamino)purin-9-yl]oxolane-3,4-diol Chemical compound N1=C([C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C3=NC(NCCN4CCCCC4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)N=NN1C1CCC1 VSPPBGVEBYWNIY-CTMYTVLESA-N 0.000 claims 1
- KCTJKXHHQWMHOF-CKXMCULTSA-N (2r,3s,4r,5r)-2-[2-(2-chloroethyl)tetrazol-5-yl]-5-[6-(2,2-diphenylethylamino)-2-(2-piperidin-1-ylethylamino)purin-9-yl]oxolane-3,4-diol Chemical compound C=1([C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C3=NC(NCCN4CCCCC4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)N=NN(CCCl)N=1 KCTJKXHHQWMHOF-CKXMCULTSA-N 0.000 claims 1
- INHNOBWXPBUJOT-CTMYTVLESA-N (2r,3s,4r,5r)-2-[2-(cyclopropylmethyl)tetrazol-5-yl]-5-[6-(2,2-diphenylethylamino)-2-(2-piperidin-1-ylethylamino)purin-9-yl]oxolane-3,4-diol Chemical compound N1=C([C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C3=NC(NCCN4CCCCC4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)N=NN1CC1CC1 INHNOBWXPBUJOT-CTMYTVLESA-N 0.000 claims 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 120
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- 239000000203 mixture Substances 0.000 description 53
- 239000000543 intermediate Substances 0.000 description 42
- 235000019439 ethyl acetate Nutrition 0.000 description 39
- 239000000243 solution Substances 0.000 description 38
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 239000007787 solid Substances 0.000 description 35
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 29
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 239000011541 reaction mixture Substances 0.000 description 26
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 21
- 210000000265 leukocyte Anatomy 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 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 18
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 18
- 239000000460 chlorine Substances 0.000 description 17
- 238000004809 thin layer chromatography Methods 0.000 description 17
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
- 239000003921 oil Substances 0.000 description 16
- 235000019198 oils Nutrition 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 13
- 239000002585 base Substances 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 11
- 239000010410 layer Substances 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 108020003175 receptors Proteins 0.000 description 10
- 102000005962 receptors Human genes 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 9
- 229960005305 adenosine Drugs 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 238000012800 visualization Methods 0.000 description 9
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 8
- 206010061218 Inflammation Diseases 0.000 description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
- 201000010099 disease Diseases 0.000 description 8
- 238000010828 elution Methods 0.000 description 8
- 239000011737 fluorine Substances 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 235000019253 formic acid Nutrition 0.000 description 8
- 230000004054 inflammatory process Effects 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000000377 silicon dioxide Substances 0.000 description 8
- 230000003110 anti-inflammatory effect Effects 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 238000004108 freeze drying Methods 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 239000008194 pharmaceutical composition Substances 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 7
- WBNQTEKLVXXLQW-MATHAZKKSA-N (3s,4r,5r)-5-(6-aminopurin-9-yl)-2,2-bis(hydroxymethyl)oxolane-3,4-diol Chemical class C1=NC=2C(N)=NC=NC=2N1[C@@H]1OC(CO)(CO)[C@@H](O)[C@H]1O WBNQTEKLVXXLQW-MATHAZKKSA-N 0.000 description 6
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 101150065749 Churc1 gene Proteins 0.000 description 6
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- 102100038239 Protein Churchill Human genes 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 6
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- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
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- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
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- 238000002953 preparative HPLC Methods 0.000 description 5
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- 230000000451 tissue damage Effects 0.000 description 5
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 241000282412 Homo Species 0.000 description 4
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
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- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- 235000011181 potassium carbonates Nutrition 0.000 description 4
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
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- 239000005695 Ammonium acetate Substances 0.000 description 3
- 241000700198 Cavia Species 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
- A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
- A61K31/7076—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines containing purines, e.g. adenosine, adenylic acid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/06—Heterocyclic radicals
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| GBGB9813538.7A GB9813538D0 (en) | 1998-06-23 | 1998-06-23 | Chemical compounds |
| GBGB9909482.3A GB9909482D0 (en) | 1999-04-23 | 1999-04-23 | 2-(Purin-9-yl)-tetahydrofuran-3,4-diol derivatives |
| PCT/EP1999/004269 WO1999067265A1 (en) | 1998-06-23 | 1999-06-23 | 2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives |
Publications (1)
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| HRP20000894A2 true HRP20000894A2 (en) | 2001-12-31 |
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| HR20000894A HRP20000894A2 (en) | 1998-06-23 | 2000-12-21 | 2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives |
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| PL (1) | PL345062A1 (pt) |
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| AR017457A1 (es) * | 1998-02-14 | 2001-09-05 | Glaxo Group Ltd | Compuestos derivados de 2-(purin-9-il)-tetrahidrofuran-3,4-diol, procesos para su preparacion, composiciones que los contienen y su uso en terapia para el tratamiento de enfermedades inflamatorias. |
| US7378400B2 (en) | 1999-02-01 | 2008-05-27 | University Of Virginia Patent Foundation | Method to reduce an inflammatory response from arthritis |
| US7427606B2 (en) | 1999-02-01 | 2008-09-23 | University Of Virginia Patent Foundation | Method to reduce inflammatory response in transplanted tissue |
| US6232297B1 (en) | 1999-02-01 | 2001-05-15 | University Of Virginia Patent Foundation | Methods and compositions for treating inflammatory response |
| NZ521633A (en) * | 2000-04-26 | 2005-01-28 | Eisai Co Ltd | Use of an adenosine A2 or A2b recpetor antagonist for promoting bowel movement |
| GB0022695D0 (en) | 2000-09-15 | 2000-11-01 | Pfizer Ltd | Purine Derivatives |
| GB0104555D0 (en) * | 2001-02-23 | 2001-04-11 | Glaxo Group Ltd | New Therapeutic method |
| CA2460911C (en) | 2001-10-01 | 2011-08-30 | University Of Virginia Patent Foundation | 2-propynyl adenosine analogs having a2a agonist activity and compositions thereof |
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| AR049384A1 (es) | 2004-05-24 | 2006-07-26 | Glaxo Group Ltd | Derivados de purina |
| US7576069B2 (en) | 2004-08-02 | 2009-08-18 | University Of Virginia Patent Foundation | 2-polycyclic propynyl adenosine analogs having A2A agonist activity |
| US7442687B2 (en) | 2004-08-02 | 2008-10-28 | The University Of Virginia Patent Foundation | 2-polycyclic propynyl adenosine analogs having A2A agonist activity |
| SG155182A1 (en) | 2004-08-02 | 2009-09-30 | Univ Virginia | 2-propynyl adenosine analogs with modified 5æ-ribose groups having a2a agonist activity |
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| DK2013211T3 (da) | 2006-04-21 | 2012-07-02 | Novartis Ag | Purinderivater til anvendelse som adenosin-A2A-receptoragonister |
| GB0607950D0 (en) | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| EP1889846A1 (en) * | 2006-07-13 | 2008-02-20 | Novartis AG | Purine derivatives as A2a agonists |
| EP1903044A1 (en) | 2006-09-14 | 2008-03-26 | Novartis AG | Adenosine Derivatives as A2A Receptor Agonists |
| EP2081933B1 (en) | 2006-09-29 | 2011-03-23 | Novartis AG | Pyrazolopyrimidines as pi3k lipid kinase inhibitors |
| RU2009120389A (ru) | 2006-10-30 | 2010-12-10 | Новартис АГ (CH) | Гетероциклические соединения в качестве противовоспалительных агентов |
| ES2442930T3 (es) | 2008-01-11 | 2014-02-14 | Novartis Ag | Pirimidinas como inhibidores de cinasas |
| DK2391366T3 (da) | 2009-01-29 | 2013-01-07 | Novartis Ag | Substituerede benzimidazoler til behandling af astrocytomer |
| US8389526B2 (en) | 2009-08-07 | 2013-03-05 | Novartis Ag | 3-heteroarylmethyl-imidazo[1,2-b]pyridazin-6-yl derivatives |
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| AU2010284254B2 (en) | 2009-08-17 | 2015-09-17 | Intellikine, Llc | Heterocyclic compounds and uses thereof |
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| WO2012034095A1 (en) | 2010-09-09 | 2012-03-15 | Irm Llc | Compounds and compositions as trk inhibitors |
| US8637516B2 (en) | 2010-09-09 | 2014-01-28 | Irm Llc | Compounds and compositions as TRK inhibitors |
| EP2673277A1 (en) | 2011-02-10 | 2013-12-18 | Novartis AG | [1, 2, 4]triazolo [4, 3 -b]pyridazine compounds as inhibitors of the c-met tyrosine kinase |
| US9127000B2 (en) | 2011-02-23 | 2015-09-08 | Intellikine, LLC. | Heterocyclic compounds and uses thereof |
| EP2678338B1 (en) | 2011-02-25 | 2015-09-09 | Novartis AG | Pyrazolo[1,5-a]pyridines as trk inhibitors |
| EP2755976B1 (en) | 2011-09-15 | 2018-07-18 | Novartis AG | 6-substituted 3-(quinolin-6-ylthio)-[1,2,4]triazolo[4,3-a]pyridines as c-met tyrosine kinase inhibitors |
| JP6130391B2 (ja) | 2011-11-23 | 2017-05-17 | インテリカイン， エルエルシー | Ｍｔｏｒ阻害剤を使用する強化された治療レジメン |
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| EP2968340A4 (en) | 2013-03-15 | 2016-08-10 | Intellikine Llc | COMBINING KINASE INHIBITORS AND USES THEREOF |
| TW201605450A (zh) | 2013-12-03 | 2016-02-16 | 諾華公司 | Ｍｄｍ２抑制劑與ＢＲＡＦ抑制劑之組合及其用途 |
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| EP3174869B1 (en) | 2014-07-31 | 2020-08-19 | Novartis AG | Combination therapy of a met inhibitor and an egfr inhibitor |
| CN106632572B (zh) * | 2016-12-16 | 2018-08-14 | 中国科学院成都生物研究所 | 一种黄芪甲苷衍生物及其制备方法和应用 |
| TW202140550A (zh) | 2020-01-29 | 2021-11-01 | 瑞士商諾華公司 | 使用抗ｔｓｌｐ抗體治療炎性或阻塞性氣道疾病之方法 |
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| BE768925A (fr) | 1970-06-30 | 1971-11-03 | Takeda Chemical Industries Ltd | Derives d'adenosine et procede de preparation |
| US4224438A (en) | 1970-07-14 | 1980-09-23 | Boehringer Mannheim Gmbh | Adenosine-5'-carboxylic acid amides |
| CA1019727A (en) | 1971-03-18 | 1977-10-25 | Abbott Laboratories | Adenosine-5'-carboxylic acid amides |
| BE789773A (fr) | 1971-10-08 | 1973-04-06 | Schering Ag | Adenosines n6 -substituees et leur procede de |
| US3864483A (en) | 1972-03-22 | 1975-02-04 | Abbott Lab | Adenosine-5{40 -carboxylic acid amides |
| CA1082695A (en) | 1972-04-10 | 1980-07-29 | Francis E. Fischer | Process for preparing adenosine-5'-carboxamides |
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-
1999
- 1999-06-23 AP APAP/P/2000/002016A patent/AP2000002016A0/en unknown
- 1999-06-23 EP EP99931113A patent/EP1090022B1/en not_active Expired - Lifetime
- 1999-06-23 ES ES99931113T patent/ES2204139T3/es not_active Expired - Lifetime
- 1999-06-23 JP JP2000555916A patent/JP3933870B2/ja not_active Expired - Fee Related
- 1999-06-23 KR KR1020007014720A patent/KR20010071591A/ko not_active Application Discontinuation
- 1999-06-23 NZ NZ509030A patent/NZ509030A/en not_active Application Discontinuation
- 1999-06-23 DE DE69910213T patent/DE69910213T2/de not_active Expired - Lifetime
- 1999-06-23 CA CA002335809A patent/CA2335809A1/en not_active Abandoned
- 1999-06-23 IL IL14039699A patent/IL140396A0/xx unknown
- 1999-06-23 BR BR9911482-8A patent/BR9911482A/pt not_active IP Right Cessation
- 1999-06-23 SK SK1954-2000A patent/SK19542000A3/sk unknown
- 1999-06-23 EE EEP200000768A patent/EE200000768A/xx unknown
- 1999-06-23 YU YU81100A patent/YU81100A/sh unknown
- 1999-06-23 TR TR2001/00410T patent/TR200100410T2/xx unknown
- 1999-06-23 PL PL99345062A patent/PL345062A1/xx unknown
- 1999-06-23 WO PCT/EP1999/004269 patent/WO1999067265A1/en not_active Application Discontinuation
- 1999-06-23 CZ CZ20004868A patent/CZ20004868A3/cs unknown
- 1999-06-23 ID IDW20010189D patent/ID29609A/id unknown
- 1999-06-23 CN CN99809892A patent/CN1313861A/zh active Pending
- 1999-06-23 AU AU47744/99A patent/AU750462B2/en not_active Ceased
- 1999-06-23 US US09/720,390 patent/US6495528B1/en not_active Expired - Fee Related
- 1999-06-23 HU HU0103025A patent/HUP0103025A3/hu unknown
- 1999-06-23 AT AT99931113T patent/ATE246701T1/de not_active IP Right Cessation
- 1999-06-23 EA EA200001224A patent/EA200001224A1/ru unknown
-
2000
- 2000-12-19 IS IS5779A patent/IS5779A/is unknown
- 2000-12-21 NO NO20006548A patent/NO20006548L/no not_active Application Discontinuation
- 2000-12-21 HR HR20000894A patent/HRP20000894A2/hr not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EA200001224A1 (ru) | 2001-08-27 |
| NO20006548D0 (no) | 2000-12-21 |
| JP2002518512A (ja) | 2002-06-25 |
| YU81100A (sh) | 2003-10-31 |
| DE69910213D1 (de) | 2003-09-11 |
| HUP0103025A3 (en) | 2002-04-29 |
| DE69910213T2 (de) | 2004-07-01 |
| EE200000768A (et) | 2002-04-15 |
| CZ20004868A3 (cs) | 2001-08-15 |
| KR20010071591A (ko) | 2001-07-28 |
| IS5779A (is) | 2000-12-19 |
| ES2204139T3 (es) | 2004-04-16 |
| NO20006548L (no) | 2001-02-22 |
| WO1999067265A1 (en) | 1999-12-29 |
| AP2000002016A0 (en) | 2000-12-31 |
| NZ509030A (en) | 2003-07-25 |
| BR9911482A (pt) | 2002-01-22 |
| CN1313861A (zh) | 2001-09-19 |
| SK19542000A3 (sk) | 2001-09-11 |
| CA2335809A1 (en) | 1999-12-29 |
| AU4774499A (en) | 2000-01-10 |
| EP1090022A1 (en) | 2001-04-11 |
| ATE246701T1 (de) | 2003-08-15 |
| JP3933870B2 (ja) | 2007-06-20 |
| EP1090022B1 (en) | 2003-08-06 |
| HUP0103025A2 (hu) | 2001-12-28 |
| TR200100410T2 (tr) | 2001-06-21 |
| ID29609A (id) | 2001-09-06 |
| AU750462B2 (en) | 2002-07-18 |
| PL345062A1 (en) | 2001-11-19 |
| US6495528B1 (en) | 2002-12-17 |
| IL140396A0 (en) | 2002-02-10 |
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