HRP20000538A2 - 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: HRP20000538A2
Authority: HR; Croatia
Prior art keywords: ethyl; ethylamino; purin; oxadiazol; furan
Prior art date: 1998-02-14

Application number

HR20000538A

Other languages

English (en)

Croatian (hr)

Inventor

David Edmund Bays

Chuen Chan

Caroline Mary Cook

Richard Peter Charles Cousins

Brian Cox

Hazel Joan Dyke

Frank Ellis

Joanna Victoria Geden

Stephen Swanson

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.)

1998-02-14

Filing date

2000-08-11

Publication date

2000-12-31

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26313119&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=HRP20000538(A2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1998-02-14 Priority claimed from GBGB9803169.3A external-priority patent/GB9803169D0/en

1998-06-23 Priority claimed from GBGB9813533.8A external-priority patent/GB9813533D0/en

2000-08-11 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

2000-12-31 Publication of HRP20000538A2 publication Critical patent/HRP20000538A2/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 233
239000000203 mixture Substances 0.000 claims description 85
-1 cyclohexylethyl Chemical group 0.000 claims description 64
238000000034 method Methods 0.000 claims description 42
239000002904 solvent Substances 0.000 claims description 38
150000003839 salts Chemical class 0.000 claims description 31
238000002360 preparation method Methods 0.000 claims description 23
239000001257 hydrogen Substances 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 21
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
125000003118 aryl group Chemical group 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 19
229910052736 halogen Inorganic materials 0.000 claims description 15
150000002367 halogens Chemical class 0.000 claims description 15
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 13
238000011282 treatment Methods 0.000 claims description 13
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
239000003814 drug Substances 0.000 claims description 10
230000008569 process Effects 0.000 claims description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
150000002431 hydrogen Chemical class 0.000 claims description 8
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 7
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
229910052717 sulfur Inorganic materials 0.000 claims description 7
125000002393 azetidinyl group Chemical group 0.000 claims description 6
125000002757 morpholinyl group Chemical group 0.000 claims description 6
125000000286 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 6
125000004193 piperazinyl group Chemical group 0.000 claims description 6
125000003386 piperidinyl group Chemical group 0.000 claims description 6
125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
208000006673 asthma Diseases 0.000 claims description 5
125000002785 azepinyl group Chemical group 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 4
229910005965 SO 2 Inorganic materials 0.000 claims description 3
239000000969 carrier Substances 0.000 claims description 3
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical group C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 claims description 3
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
WPSALBBQFLEHDL-QCUYGVNKSA-N (2r,3r,4s,5s)-2-[6-amino-2-(2-phenylethylamino)purin-9-yl]-5-(3-methyl-1,2,4-oxadiazol-5-yl)oxolane-3,4-diol Chemical compound CC1=NOC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCC=4C=CC=CC=4)=NC(N)=C3N=C2)O)=N1 WPSALBBQFLEHDL-QCUYGVNKSA-N 0.000 claims description 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
125000002877 alkyl aryl group Chemical group 0.000 claims description 2
125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 claims description 2
238000010511 deprotection reaction Methods 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
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
208000027866 inflammatory disease Diseases 0.000 claims 2
NKRGRTKDMXKVTD-SCQLIKFLSA-N (2r,3r,4s,5s)-2-[2-(3-bicyclo[2.2.1]heptanylamino)-6-(2,2-diphenylethylamino)purin-9-yl]-5-(3-ethyl-1,2,4-oxadiazol-5-yl)oxolane-3,4-diol Chemical compound CCC1=NOC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NC4C5CCC(C5)C4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 NKRGRTKDMXKVTD-SCQLIKFLSA-N 0.000 claims 1
SRRASVGMZCJTCB-RQXXJAGISA-N (2r,3r,4s,5s)-2-[2-[2-(1-methylimidazol-4-yl)ethylamino]-6-(pentan-3-ylamino)purin-9-yl]-5-(3-methyl-1,2,4-oxadiazol-5-yl)oxolane-3,4-diol Chemical compound N=1C=2N([C@H]3[C@@H]([C@H](O)[C@H](O3)C=3ON=C(C)N=3)O)C=NC=2C(NC(CC)CC)=NC=1NCCC1=CN(C)C=N1 SRRASVGMZCJTCB-RQXXJAGISA-N 0.000 claims 1
MYYPCGXBKDGTRC-BSYZOHBLSA-N (2r,3r,4s,5s)-2-[2-[2-(3,4-dimethoxyphenyl)ethylamino]-6-(2,2-diphenylethylamino)purin-9-yl]-5-(3-ethyl-1,2,4-oxadiazol-5-yl)oxolane-3,4-diol Chemical compound CCC1=NOC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCC=4C=C(OC)C(OC)=CC=4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 MYYPCGXBKDGTRC-BSYZOHBLSA-N 0.000 claims 1
WUAZHJCFTVTRIX-NLJXWPIHSA-N (2r,3r,4s,5s)-2-[6-(2,2-diphenylethylamino)-2-(2-hydroxyethylamino)purin-9-yl]-5-(3-ethyl-1,2,4-oxadiazol-5-yl)oxolane-3,4-diol Chemical compound CCC1=NOC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCO)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 WUAZHJCFTVTRIX-NLJXWPIHSA-N 0.000 claims 1
FSECLRZQTWIQFG-CKXMCULTSA-N (2r,3r,4s,5s)-2-[6-(2,2-diphenylethylamino)-2-(2-morpholin-4-ylethylamino)purin-9-yl]-5-(3-ethyl-1,2,4-oxadiazol-5-yl)oxolane-3,4-diol Chemical compound CCC1=NOC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCN4CCOCC4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 FSECLRZQTWIQFG-CKXMCULTSA-N 0.000 claims 1
POVHKPRNQLEWIS-CKXMCULTSA-N (2r,3r,4s,5s)-2-[6-(2,2-diphenylethylamino)-2-(2-pyrrolidin-1-ylethylamino)purin-9-yl]-5-(3-ethyl-1,2,4-oxadiazol-5-yl)oxolane-3,4-diol Chemical compound CCC1=NOC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCN4CCCC4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 POVHKPRNQLEWIS-CKXMCULTSA-N 0.000 claims 1
AITGNWRETVKUSV-CKXMCULTSA-N (2r,3r,4s,5s)-2-[6-(2,2-diphenylethylamino)-2-(4-fluoroanilino)purin-9-yl]-5-(3-ethyl-1,2,4-oxadiazol-5-yl)oxolane-3,4-diol Chemical compound CCC1=NOC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NC=4C=CC(F)=CC=4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 AITGNWRETVKUSV-CKXMCULTSA-N 0.000 claims 1
AVWUFQCCUSAKRU-CKXMCULTSA-N (2r,3r,4s,5s)-2-[6-(2,2-diphenylethylamino)-2-[2-(1-methylimidazol-4-yl)ethylamino]purin-9-yl]-5-(3-ethyl-1,2,4-oxadiazol-5-yl)oxolane-3,4-diol Chemical compound CCC1=NOC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCC=4N=CN(C)C=4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 AVWUFQCCUSAKRU-CKXMCULTSA-N 0.000 claims 1
MRAHZKUIBFCWHI-OVDFTCDZSA-N (2r,3r,4s,5s)-2-[6-(2,2-diphenylethylamino)-2-[2-(1-methylimidazol-4-yl)ethylamino]purin-9-yl]-5-(3-methyl-1,2,4-oxadiazol-5-yl)oxolane-3,4-diol Chemical compound CC1=NOC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCC=4N=CN(C)C=4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 MRAHZKUIBFCWHI-OVDFTCDZSA-N 0.000 claims 1
YEOGFUMTTLLPLS-KCIBBDPESA-N (2r,3r,4s,5s)-2-[6-(2,2-diphenylethylamino)-2-[2-(1-methylimidazol-4-yl)ethylamino]purin-9-yl]-5-(3-propyl-1,2,4-oxadiazol-5-yl)oxolane-3,4-diol Chemical compound CCCC1=NOC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCC=4N=CN(C)C=4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 YEOGFUMTTLLPLS-KCIBBDPESA-N 0.000 claims 1
DQKSTTLTWONLHD-YRIIQKNPSA-N (2r,3r,4s,5s)-2-[6-(2,2-diphenylethylamino)-2-[2-(1h-imidazol-5-yl)ethylamino]purin-9-yl]-5-(3-methyl-1,2,4-oxadiazol-5-yl)oxolane-3,4-diol Chemical compound CC1=NOC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCC=4N=CNC=4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 DQKSTTLTWONLHD-YRIIQKNPSA-N 0.000 claims 1
ISTWUZFHTOFWKT-KCIBBDPESA-N (2r,3r,4s,5s)-2-[6-(2,2-diphenylethylamino)-2-[2-(pyridin-2-ylamino)ethylamino]purin-9-yl]-5-(3-ethyl-1,2,4-oxadiazol-5-yl)oxolane-3,4-diol Chemical compound CCC1=NOC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCNC=4N=CC=CC=4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 ISTWUZFHTOFWKT-KCIBBDPESA-N 0.000 claims 1
WVOFRWNZROYJPW-QCUYGVNKSA-N (2r,3r,4s,5s)-2-[6-amino-2-(2-pyridin-2-ylethylamino)purin-9-yl]-5-(3-ethyl-1,2,4-oxadiazol-5-yl)oxolane-3,4-diol Chemical compound CCC1=NOC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCC=4N=CC=CC=4)=NC(N)=C3N=C2)O)=N1 WVOFRWNZROYJPW-QCUYGVNKSA-N 0.000 claims 1
XVUSYJSTYSYFSI-MOROJQBDSA-N (2r,3r,4s,5s)-2-[6-amino-2-(2-pyridin-2-ylethylamino)purin-9-yl]-5-(3-methyl-1,2,4-oxadiazol-5-yl)oxolane-3,4-diol Chemical compound CC1=NOC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCC=4N=CC=CC=4)=NC(N)=C3N=C2)O)=N1 XVUSYJSTYSYFSI-MOROJQBDSA-N 0.000 claims 1
DIXGEJBUYLVVAE-MEQWQQMJSA-N (2r,3r,4s,5s)-2-[6-amino-2-(cyclopentylamino)purin-9-yl]-5-(3-methyl-1,2,4-oxadiazol-5-yl)oxolane-3,4-diol Chemical compound CC1=NOC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NC4CCCC4)=NC(N)=C3N=C2)O)=N1 DIXGEJBUYLVVAE-MEQWQQMJSA-N 0.000 claims 1
GZKIEROUODOYHD-MOROJQBDSA-N (2r,3r,4s,5s)-2-[6-amino-2-[2-(1-methylimidazol-4-yl)ethylamino]purin-9-yl]-5-(3-ethyl-1,2,4-oxadiazol-5-yl)oxolane-3,4-diol Chemical compound CCC1=NOC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCC=4N=CN(C)C=4)=NC(N)=C3N=C2)O)=N1 GZKIEROUODOYHD-MOROJQBDSA-N 0.000 claims 1
ZHOALVOEEGGODX-PFHKOEEOSA-N (2r,3r,4s,5s)-2-[6-amino-2-[2-(1-methylimidazol-4-yl)ethylamino]purin-9-yl]-5-(3-methyl-1,2,4-oxadiazol-5-yl)oxolane-3,4-diol Chemical compound CC1=NOC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCC=4N=CN(C)C=4)=NC(N)=C3N=C2)O)=N1 ZHOALVOEEGGODX-PFHKOEEOSA-N 0.000 claims 1
JKHXBPSGTMDVQB-UAKAABGRSA-N (2s,3s,4r,5r)-2-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-5-[2-[2-(1-methylimidazol-4-yl)ethylamino]-6-(pentan-3-ylamino)purin-9-yl]oxolane-3,4-diol Chemical compound N=1C=2N([C@H]3[C@@H]([C@H](O)[C@H](O3)C=3ON=C(N=3)C3CC3)O)C=NC=2C(NC(CC)CC)=NC=1NCCC1=CN(C)C=N1 JKHXBPSGTMDVQB-UAKAABGRSA-N 0.000 claims 1
XUIPSYYBPYMDAL-PBQROFAYSA-N (2s,3s,4r,5r)-2-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-5-[6-(pentan-3-ylamino)-2-(2-pyridin-2-ylethylamino)purin-9-yl]oxolane-3,4-diol Chemical compound N=1C=2N([C@H]3[C@@H]([C@H](O)[C@H](O3)C=3ON=C(N=3)C3CC3)O)C=NC=2C(NC(CC)CC)=NC=1NCCC1=CC=CC=N1 XUIPSYYBPYMDAL-PBQROFAYSA-N 0.000 claims 1
OYUNKFFEXRBXPK-QPXQOZNCSA-N (2s,3s,4r,5r)-2-(3-ethyl-1,2,4-oxadiazol-5-yl)-5-[2-[2-(1-methylimidazol-4-yl)ethylamino]-6-(pentan-3-ylamino)purin-9-yl]oxolane-3,4-diol Chemical compound N=1C=2N([C@H]3[C@@H]([C@H](O)[C@H](O3)C=3ON=C(CC)N=3)O)C=NC=2C(NC(CC)CC)=NC=1NCCC1=CN(C)C=N1 OYUNKFFEXRBXPK-QPXQOZNCSA-N 0.000 claims 1
YMBDYWWPIUCDRO-QPXQOZNCSA-N (2s,3s,4r,5r)-2-(3-methyl-1,2,4-oxadiazol-5-yl)-5-[6-(pentan-3-ylamino)-2-(2-piperidin-1-ylethylamino)purin-9-yl]oxolane-3,4-diol Chemical compound N=1C=2N([C@H]3[C@@H]([C@H](O)[C@H](O3)C=3ON=C(C)N=3)O)C=NC=2C(NC(CC)CC)=NC=1NCCN1CCCCC1 YMBDYWWPIUCDRO-QPXQOZNCSA-N 0.000 claims 1
NPSCLFVCPQPJCL-CUCOOGOQSA-N CCC1=NOC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(N[C@@H]4CC[C@@H](N)CC4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 Chemical compound CCC1=NOC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(N[C@@H]4CC[C@@H](N)CC4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 NPSCLFVCPQPJCL-CUCOOGOQSA-N 0.000 claims 1
KCLAINNQDIJBHU-VLJMVEFDSA-N N=1C=2N([C@H]3[C@@H]([C@H](O)[C@H](O3)C=3ON=C(C)N=3)O)C=NC=2C(NC(CC)CC)=NC=1N[C@H]1CC[C@H](N)CC1 Chemical compound N=1C=2N([C@H]3[C@@H]([C@H](O)[C@H](O3)C=3ON=C(C)N=3)O)C=NC=2C(NC(CC)CC)=NC=1N[C@H]1CC[C@H](N)CC1 KCLAINNQDIJBHU-VLJMVEFDSA-N 0.000 claims 1
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239000012304 carboxyl activating agent Substances 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
239000000825 pharmaceutical preparation Substances 0.000 claims 1
239000000543 intermediate Substances 0.000 description 125
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 104
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238000004895 liquid chromatography mass spectrometry Methods 0.000 description 79
239000007787 solid Substances 0.000 description 76
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 70
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 53
239000000243 solution Substances 0.000 description 52
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
238000004128 high performance liquid chromatography Methods 0.000 description 43
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
238000004108 freeze drying Methods 0.000 description 36
235000019439 ethyl acetate Nutrition 0.000 description 35
239000000377 silicon dioxide Substances 0.000 description 34
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
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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 32
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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
- 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
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- 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]
- 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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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Molecular Biology (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
Genetics & Genomics (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Pulmonology (AREA)
Dermatology (AREA)
Psychiatry (AREA)
Rheumatology (AREA)
Pain & Pain Management (AREA)
Hospice & Palliative Care (AREA)
Epidemiology (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)

HR20000538A 1998-02-14 2000-08-11 2-(purin-9-yl) tetrahydrofuran-3,4-diol derivatives HRP20000538A2 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GBGB9803169.3A GB9803169D0 (en)	1998-02-14	1998-02-14	Chemical compounds
GBGB9813533.8A GB9813533D0 (en)	1998-06-23	1998-06-23	Chemical compounds
PCT/EP1999/000915 WO1999041267A1 (en)	1998-02-14	1999-02-12	2-(purin-9-yl) -tetrahydrofuran-3, 4-diol derivatives

Publications (1)

Publication Number	Publication Date
HRP20000538A2 true HRP20000538A2 (en)	2000-12-31

Family

ID=26313119

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR20000538A HRP20000538A2 (en)	1998-02-14	2000-08-11	2-(purin-9-yl) tetrahydrofuran-3,4-diol derivatives

Country Status (32)

Country	Link
US (1)	US6610665B1 (pt)
EP (1)	EP1056759B1 (pt)
JP (1)	JP2002503669A (pt)
KR (1)	KR20010082512A (pt)
AP (1)	AP2000001881A0 (pt)
AR (1)	AR017457A1 (pt)
AT (1)	ATE223429T1 (pt)
AU (1)	AU757156B2 (pt)
BR (1)	BR9907886A (pt)
CA (1)	CA2319009A1 (pt)
CO (1)	CO4990969A1 (pt)
DE (1)	DE69902758T2 (pt)
DK (1)	DK1056759T3 (pt)
EA (1)	EA200000759A1 (pt)
EE (1)	EE200000358A (pt)
ES (1)	ES2183516T3 (pt)
HK (1)	HK1032062A1 (pt)
HR (1)	HRP20000538A2 (pt)
HU (1)	HUP0100702A3 (pt)
IL (1)	IL137402A0 (pt)
IS (1)	IS5576A (pt)
MA (1)	MA27121A1 (pt)
NO (1)	NO20004045D0 (pt)
NZ (1)	NZ505812A (pt)
PE (1)	PE20000270A1 (pt)
PL (1)	PL342396A1 (pt)
PT (1)	PT1056759E (pt)
SK (1)	SK12002000A3 (pt)
SV (1)	SV1999000016A (pt)
TR (1)	TR200002355T2 (pt)
WO (1)	WO1999041267A1 (pt)
YU (1)	YU50800A (pt)

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US6495528B1 (en) *	1998-06-23	2002-12-17	Smithkline Beecham Corporation	2-(Purin -9-yl)-tetrahydrofuran-3,4-diol derivatives
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NZ532062A (en)	2001-10-01	2006-09-29	Univ Virginia	2-propynyl adenosine analogues having A2 adenosine recepter agonist activity and compositions thereof to treat inflammatory responses
TW200519106A (en)	2003-05-02	2005-06-16	Novartis Ag	Organic compounds
US6930093B2 (en) *	2003-07-10	2005-08-16	Valeant Research & Development	Use of ribofuranose derivatives against inflammatory bowel diseases
GB0401334D0 (en)	2004-01-21	2004-02-25	Novartis Ag	Organic compounds
TWI346109B (en) *	2004-04-30	2011-08-01	Otsuka Pharma Co Ltd	4-amino-5-cyanopyrimidine derivatives
GB0411056D0 (en)	2004-05-18	2004-06-23	Novartis Ag	Organic compounds
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US7442687B2 (en)	2004-08-02	2008-10-28	The University Of Virginia Patent Foundation	2-polycyclic propynyl adenosine analogs having A2A agonist activity
WO2006015357A2 (en)	2004-08-02	2006-02-09	University Of Virginia Patent Foundation	2-propynyl adenosine analogs with modified 5'-ribose groups having a2a agonist activity
WO2006028618A1 (en)	2004-08-02	2006-03-16	University Of Virginia Patent Foundation	2-polycyclic propynyl adenosine analogs with modified 5'-ribose groups having a2a agonist activity
GB0424284D0 (en)	2004-11-02	2004-12-01	Novartis Ag	Organic compounds
GB0426164D0 (en)	2004-11-29	2004-12-29	Novartis Ag	Organic compounds
GB0510390D0 (en)	2005-05-20	2005-06-29	Novartis Ag	Organic compounds
GB0514809D0 (en)	2005-07-19	2005-08-24	Glaxo Group Ltd	Compounds
AR058104A1 (es)	2005-10-21	2008-01-23	Novartis Ag	Compuestos organicos
GB0601951D0 (en)	2006-01-31	2006-03-15	Novartis Ag	Organic compounds
JP2010504933A (ja)	2006-09-29	2010-02-18	ノバルティスアーゲー	Ｐｉ３ｋ脂質キナーゼ阻害剤としてのピラゾロピリミジン
EP2089393A1 (en)	2006-10-30	2009-08-19	Novartis AG	Heterocyclic compounds as antiinflammatory agents
PL2231642T3 (pl)	2008-01-11	2014-04-30	Novartis Ag	Pirymidyny jako inhibitory kinazy
US20110281917A1 (en)	2009-01-29	2011-11-17	Darrin Stuart	Substituted Benzimidazoles for the Treatment of Astrocytomas
US8389526B2 (en)	2009-08-07	2013-03-05	Novartis Ag	3-heteroarylmethyl-imidazo[1,2-b]pyridazin-6-yl derivatives
AU2010283806A1 (en)	2009-08-12	2012-03-01	Novartis Ag	Heterocyclic hydrazone compounds and their uses to treat cancer and inflammation
SG178454A1 (en)	2009-08-17	2012-03-29	Intellikine Inc	Heterocyclic compounds and uses thereof
JP5775871B2 (ja)	2009-08-20	2015-09-09	ノバルティスアーゲー	ヘテロ環式オキシム化合物
UY33597A (es)	2010-09-09	2012-04-30	Irm Llc	Compuestos y composiciones como inhibidores de la trk
WO2012034095A1 (en)	2010-09-09	2012-03-15	Irm Llc	Compounds and compositions as trk inhibitors
WO2012107500A1 (en)	2011-02-10	2012-08-16	Novartis Ag	[1, 2, 4] triazolo [4, 3 -b] pyridazine compounds as inhibitors of the c-met tyrosine kinase
WO2012116237A2 (en)	2011-02-23	2012-08-30	Intellikine, Llc	Heterocyclic compounds and uses thereof
WO2012116217A1 (en)	2011-02-25	2012-08-30	Irm Llc	Compounds and compositions as trk inhibitors
JP5957526B2 (ja)	2011-09-15	2016-07-27	ノバルティスアーゲー	チロシンキナーゼとしての６−置換３−（キノリン−６−イルチオ）−［１，２，４］トリアゾロ［４，３−ａ］ピラジン
WO2013078440A2 (en)	2011-11-23	2013-05-30	Intellikine, Llc	Enhanced treatment regimens using mtor inhibitors
CN110507654A (zh)	2012-04-03	2019-11-29	诺华有限公司	有酪氨酸激酶抑制剂的组合产品和其应用
JP2016512835A (ja)	2013-03-15	2016-05-09	インテリカイン，エルエルシー	キナーゼ阻害剤の組み合わせ及びそれらの使用
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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US10195208B2 (en)	2014-07-31	2019-02-05	Novartis Ag	Combination therapy
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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TW528755B (en) *	1996-12-24	2003-04-21	Glaxo Group Ltd	2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives
CO4990969A1 (es) *	1998-02-14	2000-12-26	Glaxo Group Ltd	Derivados de 2-(purin-9-il)-tetrahidrofuran-3,4-diol
US6495528B1 (en) *	1998-06-23	2002-12-17	Smithkline Beecham Corporation	2-(Purin -9-yl)-tetrahydrofuran-3,4-diol derivatives

1999
- 1999-02-11 CO CO99008188A patent/CO4990969A1/es unknown
- 1999-02-11 AR ARP990100570A patent/AR017457A1/es active IP Right Grant
- 1999-02-11 PE PE1999000123A patent/PE20000270A1/es not_active Application Discontinuation
- 1999-02-12 US US09/622,313 patent/US6610665B1/en not_active Expired - Fee Related
- 1999-02-12 SV SV1999000016A patent/SV1999000016A/es not_active Application Discontinuation
- 1999-02-12 AU AU26235/99A patent/AU757156B2/en not_active Ceased
- 1999-02-12 TR TR2000/02355T patent/TR200002355T2/xx unknown
- 1999-02-12 KR KR1020007008866A patent/KR20010082512A/ko not_active Application Discontinuation
- 1999-02-12 PL PL99342396A patent/PL342396A1/xx unknown
- 1999-02-12 EP EP99906229A patent/EP1056759B1/en not_active Expired - Lifetime
- 1999-02-12 PT PT99906229T patent/PT1056759E/pt unknown
- 1999-02-12 MA MA25462A patent/MA27121A1/fr unknown
- 1999-02-12 BR BR9907886-4A patent/BR9907886A/pt not_active IP Right Cessation
- 1999-02-12 IL IL13740299A patent/IL137402A0/xx unknown
- 1999-02-12 DE DE69902758T patent/DE69902758T2/de not_active Expired - Fee Related
- 1999-02-12 EE EEP200000358A patent/EE200000358A/xx unknown
- 1999-02-12 DK DK99906229T patent/DK1056759T3/da active
- 1999-02-12 SK SK1200-2000A patent/SK12002000A3/sk unknown
- 1999-02-12 ES ES99906229T patent/ES2183516T3/es not_active Expired - Lifetime
- 1999-02-12 WO PCT/EP1999/000915 patent/WO1999041267A1/en not_active Application Discontinuation
- 1999-02-12 CA CA002319009A patent/CA2319009A1/en not_active Abandoned
- 1999-02-12 EA EA200000759A patent/EA200000759A1/ru unknown
- 1999-02-12 JP JP2000531459A patent/JP2002503669A/ja active Pending
- 1999-02-12 YU YU50800A patent/YU50800A/sh unknown
- 1999-02-12 HU HU0100702A patent/HUP0100702A3/hu unknown
- 1999-02-12 NZ NZ505812A patent/NZ505812A/en unknown
- 1999-02-12 AT AT99906229T patent/ATE223429T1/de not_active IP Right Cessation
- 1999-02-12 AP APAP/P/2000/001881A patent/AP2000001881A0/en unknown
2000
- 2000-07-25 IS IS5576A patent/IS5576A/is unknown
- 2000-08-11 NO NO20004045A patent/NO20004045D0/no unknown
- 2000-08-11 HR HR20000538A patent/HRP20000538A2/hr not_active Application Discontinuation
2001
- 2001-04-10 HK HK01102563A patent/HK1032062A1/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
KR20010082512A (ko)	2001-08-30
EP1056759A1 (en)	2000-12-06
DK1056759T3 (da)	2003-01-06
PE20000270A1 (es)	2000-05-20
PL342396A1 (en)	2001-06-04
HUP0100702A3 (en)	2003-01-28
ES2183516T3 (es)	2003-03-16
AP2000001881A0 (en)	2000-09-30
SV1999000016A (es)	1999-10-27
CO4990969A1 (es)	2000-12-26
TR200002355T2 (tr)	2000-11-21
MA27121A1 (fr)	2005-01-03
IS5576A (is)	2000-07-25
SK12002000A3 (sk)	2001-07-10
CA2319009A1 (en)	1999-08-19
DE69902758D1 (de)	2002-10-10
NO20004045L (no)	2000-08-11
YU50800A (sh)	2003-04-30
HK1032062A1 (en)	2001-07-06
US6610665B1 (en)	2003-08-26
ATE223429T1 (de)	2002-09-15
JP2002503669A (ja)	2002-02-05
AU757156B2 (en)	2003-02-06
DE69902758T2 (de)	2003-05-15
WO1999041267A1 (en)	1999-08-19
EA200000759A1 (ru)	2001-04-23
EP1056759B1 (en)	2002-09-04
NO20004045D0 (no)	2000-08-11
NZ505812A (en)	2002-03-01
AR017457A1 (es)	2001-09-05
HUP0100702A2 (hu)	2002-01-28
PT1056759E (pt)	2003-01-31
BR9907886A (pt)	2000-10-17
EE200000358A (et)	2001-10-15
IL137402A0 (en)	2001-07-24
AU2623599A (en)	1999-08-30

Legal Events

Date	Code	Title	Description
2000-12-31	A1OB	Publication of a patent application
2001-04-30	ARAI	Request for the grant of a patent on the basis of the submitted results of a substantive examination of a patent application
2003-01-09	ODRP	Renewal fee for the maintenance of a patent	Payment date: 20030109 Year of fee payment: 5
2008-11-18	OBST	Application withdrawn

Publication	Publication Date	Title
HRP20000538A2 (en)	2000-12-31	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
EP1090022B1 (en)	2003-08-06	2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives
EP1090020B1 (en)	2003-11-05	2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives
EP1090023B1 (en)	2003-09-10	2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives
EP1090021B1 (en)	2003-09-10	2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives
HRP20000511A2 (en)	2000-12-31	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
MXPA00012926A (en)	2002-05-09	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