HRP20000894A2 - 2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives - Google Patents

2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives Download PDF

Info

Publication number: HRP20000894A2
Authority: HR; Croatia
Prior art keywords: formula; compound represented; image; ethylamino; alkyl
Prior art date: 1998-06-23

Application number

HR20000894A

Other languages

English (en)

Croatian (hr)

Inventor

David George Allen

Chuen Chan

Richard Peter Charles Cousins

Brian Cox

Joanna Victoria Geden

Heather Hobbs

Suzanne Elaine Keeling

Alison Judith Redgrave

Thomas Davis Roper

Shiping Xie

Original Assignee

Glaxo Group Ltd

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.)

1998-06-23

Filing date

2000-12-21

Publication date

2001-12-31

1998-06-23 Priority claimed from GBGB9813538.7A external-priority patent/GB9813538D0/en

1999-04-23 Priority claimed from GBGB9909482.3A external-priority patent/GB9909482D0/en

2000-12-21 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

2001-12-31 Publication of HRP20000894A2 publication Critical patent/HRP20000894A2/hr

Links

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
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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
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239000002244 precipitate Substances 0.000 description 8
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238000004108 freeze drying Methods 0.000 description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
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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
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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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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
239000000725 suspension Substances 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
210000001519 tissue Anatomy 0.000 description 6
238000005160 1H NMR spectroscopy Methods 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
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125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
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230000008901 benefit Effects 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
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VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 5
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150000003536 tetrazoles Chemical class 0.000 description 5
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OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
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TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
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UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
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125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
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239000001593 sorbitan monooleate Substances 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
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239000003381 stabilizer Substances 0.000 description 1
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229940116362 tragacanth Drugs 0.000 description 1
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YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
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229910052905 tridymite Inorganic materials 0.000 description 1
SIOVKLKJSOKLIF-HJWRWDBZSA-N trimethylsilyl (1z)-n-trimethylsilylethanimidate Chemical compound C[Si](C)(C)OC(/C)=N\[Si](C)(C)C SIOVKLKJSOKLIF-HJWRWDBZSA-N 0.000 description 1
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Classifications

- 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
- 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
- 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
- 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]
- 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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Molecular Biology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Biochemistry (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Epidemiology (AREA)
Immunology (AREA)
Pulmonology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Transplantation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

HR20000894A 1998-06-23 2000-12-21 2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives HRP20000894A2 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
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)

Publication Number	Publication Date
HRP20000894A2 true HRP20000894A2 (en)	2001-12-31

Family

ID=26313917

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR20000894A HRP20000894A2 (en)	1998-06-23	2000-12-21	2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives

Country Status (27)

Country	Link
US (1)	US6495528B1 (pt)
EP (1)	EP1090022B1 (pt)
JP (1)	JP3933870B2 (pt)
KR (1)	KR20010071591A (pt)
CN (1)	CN1313861A (pt)
AP (1)	AP2000002016A0 (pt)
AT (1)	ATE246701T1 (pt)
AU (1)	AU750462B2 (pt)
BR (1)	BR9911482A (pt)
CA (1)	CA2335809A1 (pt)
CZ (1)	CZ20004868A3 (pt)
DE (1)	DE69910213T2 (pt)
EA (1)	EA200001224A1 (pt)
EE (1)	EE200000768A (pt)
ES (1)	ES2204139T3 (pt)
HR (1)	HRP20000894A2 (pt)
HU (1)	HUP0103025A3 (pt)
ID (1)	ID29609A (pt)
IL (1)	IL140396A0 (pt)
IS (1)	IS5779A (pt)
NO (1)	NO20006548L (pt)
NZ (1)	NZ509030A (pt)
PL (1)	PL345062A1 (pt)
SK (1)	SK19542000A3 (pt)
TR (1)	TR200100410T2 (pt)
WO (1)	WO1999067265A1 (pt)
YU (1)	YU81100A (pt)

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1999
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EE200000768A (et)	2002-04-15
HUP0103025A3 (en)	2002-04-29
IS5779A (is)	2000-12-19
BR9911482A (pt)	2002-01-22
DE69910213D1 (de)	2003-09-11
AU4774499A (en)	2000-01-10
CN1313861A (zh)	2001-09-19
SK19542000A3 (sk)	2001-09-11
AU750462B2 (en)	2002-07-18
WO1999067265A1 (en)	1999-12-29
US6495528B1 (en)	2002-12-17
JP2002518512A (ja)	2002-06-25
HUP0103025A2 (hu)	2001-12-28
DE69910213T2 (de)	2004-07-01
NO20006548D0 (no)	2000-12-21
JP3933870B2 (ja)	2007-06-20
NO20006548L (no)	2001-02-22
EA200001224A1 (ru)	2001-08-27
CA2335809A1 (en)	1999-12-29
IL140396A0 (en)	2002-02-10
ID29609A (id)	2001-09-06
EP1090022B1 (en)	2003-08-06
EP1090022A1 (en)	2001-04-11
AP2000002016A0 (en)	2000-12-31
NZ509030A (en)	2003-07-25
YU81100A (sh)	2003-10-31
CZ20004868A3 (cs)	2001-08-15
KR20010071591A (ko)	2001-07-28
ES2204139T3 (es)	2004-04-16
PL345062A1 (en)	2001-11-19
ATE246701T1 (de)	2003-08-15
TR200100410T2 (tr)	2001-06-21

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Publication	Publication Date	Title
HRP20000894A2 (en)	2001-12-31	2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives
JP4156035B2 (ja)	2008-09-24	２−（プリン−９−イル）−テトラヒドロフラン−３，４−ジオール誘導体
US6610665B1 (en)	2003-08-26	2-(purin-9-yl)-tetrahydrofuran-3, 4-diol derivatives
DE69903708T2 (de)	2003-07-03	2-(purin-9-yl)-tetrahydrofuran-3,4-diol-derivate
HRP20000895A2 (en)	2001-10-31	2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives
EP1090021A1 (en)	2001-04-11	2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives
JP2002518510A (ja)	2002-06-25	２−（プリン−９−イル）−テトラヒドロフラン−３，４−ジオール誘導体
MXPA00012926A (en)	2002-05-09	2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives
MXPA00007793A (en)	2001-11-21	2-(purin-9-yl) -tetrahydrofuran-3, 4-diol derivatives
MXPA00012895A (en)	2001-09-07	2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives
MXPA99005888A (en)	2000-01-01	2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives
CZ20002974A3 (cs)	2001-05-16	2-(purin-9-yl)-tetrahydrofuran-3,4-diolové deriváty
CZ20004870A3 (cs)	2001-06-13	2 (Purin 9 yl) tetrahydrofuran 3,4 diolové deriváty