HRP20020676A2 - Purine derivatives - Google Patents
Purine derivativesInfo
- Publication number
- HRP20020676A2 HRP20020676A2 HRP20020676A HRP20020676A2 HR P20020676 A2 HRP20020676 A2 HR P20020676A2 HR P20020676 A HRP20020676 A HR P20020676A HR P20020676 A2 HRP20020676 A2 HR P20020676A2
- Authority
- HR
- Croatia
- Prior art keywords
- formula
- compound
- amino
- alkyl
- image
- Prior art date
Links
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 title description 3
- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 234
- 238000002360 preparation method Methods 0.000 claims description 103
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 98
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 90
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 87
- 238000000034 method Methods 0.000 claims description 79
- 125000000579 2,2-diphenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 claims description 74
- 150000003839 salts Chemical class 0.000 claims description 49
- -1 OR3 Chemical group 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 42
- 125000006239 protecting group Chemical group 0.000 claims description 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 239000012453 solvate Substances 0.000 claims description 26
- 125000003386 piperidinyl group Chemical group 0.000 claims description 24
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 21
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 20
- 125000001153 fluoro group Chemical group F* 0.000 claims description 20
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 150000001412 amines Chemical class 0.000 claims description 17
- 241000124008 Mammalia Species 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 125000001624 naphthyl group Chemical group 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 claims description 12
- 238000010511 deprotection reaction Methods 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 10
- 208000007882 Gastritis Diseases 0.000 claims description 10
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 10
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 10
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 10
- 208000010668 atopic eczema Diseases 0.000 claims description 10
- 206010006451 bronchitis Diseases 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- 101150051188 Adora2a gene Proteins 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- RMFWVOLULURGJI-UHFFFAOYSA-N 2,6-dichloro-7h-purine Chemical compound ClC1=NC(Cl)=C2NC=NC2=N1 RMFWVOLULURGJI-UHFFFAOYSA-N 0.000 claims description 7
- 208000006673 asthma Diseases 0.000 claims description 7
- 230000007062 hydrolysis Effects 0.000 claims description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 7
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
- 241000894006 Bacteria Species 0.000 claims description 6
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 6
- 230000005494 condensation Effects 0.000 claims description 6
- 230000006378 damage Effects 0.000 claims description 6
- 150000002825 nitriles Chemical class 0.000 claims description 6
- 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 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 229940044601 receptor agonist Drugs 0.000 claims description 6
- 239000000018 receptor agonist Substances 0.000 claims description 6
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 5
- 201000006474 Brain Ischemia Diseases 0.000 claims description 5
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 5
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 5
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 5
- 206010009137 Chronic sinusitis Diseases 0.000 claims description 5
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 5
- 208000011231 Crohn disease Diseases 0.000 claims description 5
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 5
- 201000004624 Dermatitis Diseases 0.000 claims description 5
- 206010012434 Dermatitis allergic Diseases 0.000 claims description 5
- 206010014561 Emphysema Diseases 0.000 claims description 5
- 208000010228 Erectile Dysfunction Diseases 0.000 claims description 5
- 206010020772 Hypertension Diseases 0.000 claims description 5
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
- 201000004681 Psoriasis Diseases 0.000 claims description 5
- 208000028017 Psychotic disease Diseases 0.000 claims description 5
- 206010063837 Reperfusion injury Diseases 0.000 claims description 5
- 206010040070 Septic Shock Diseases 0.000 claims description 5
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 5
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 5
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 5
- 201000008937 atopic dermatitis Diseases 0.000 claims description 5
- 201000009267 bronchiectasis Diseases 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 206010008118 cerebral infarction Diseases 0.000 claims description 5
- 208000007451 chronic bronchitis Diseases 0.000 claims description 5
- 201000009151 chronic rhinitis Diseases 0.000 claims description 5
- 208000027157 chronic rhinosinusitis Diseases 0.000 claims description 5
- 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 5
- 206010012601 diabetes mellitus Diseases 0.000 claims description 5
- 206010015037 epilepsy Diseases 0.000 claims description 5
- 210000005095 gastrointestinal system Anatomy 0.000 claims description 5
- 201000001881 impotence Diseases 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 5
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
- 206010039083 rhinitis Diseases 0.000 claims description 5
- 230000036303 septic shock Effects 0.000 claims description 5
- 230000029663 wound healing Effects 0.000 claims description 5
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 4
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 4
- 101100134922 Gallus gallus COR5 gene Proteins 0.000 claims description 4
- 208000018262 Peripheral vascular disease Diseases 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 210000002345 respiratory system Anatomy 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000006308 propyl amino group Chemical group 0.000 claims description 3
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- WNWVKZTYMQWFHE-UHFFFAOYSA-N 4-ethylmorpholine Chemical group [CH2]CN1CCOCC1 WNWVKZTYMQWFHE-UHFFFAOYSA-N 0.000 claims description 2
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 238000005910 aminocarbonylation reaction Methods 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000002393 azetidinyl group Chemical group 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 208000027866 inflammatory disease Diseases 0.000 claims description 2
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims 5
- 229940079593 drug Drugs 0.000 claims 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 238000006136 alcoholysis reaction Methods 0.000 claims 1
- 239000012752 auxiliary agent Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 117
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 110
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
- 239000002904 solvent Substances 0.000 description 65
- 238000005160 1H NMR spectroscopy Methods 0.000 description 64
- 239000000243 solution Substances 0.000 description 59
- 239000000203 mixture Substances 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
- 238000010992 reflux Methods 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 12
- 239000006260 foam Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 210000000440 neutrophil Anatomy 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- 239000012299 nitrogen atmosphere Substances 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000010898 silica gel chromatography Methods 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 238000004809 thin layer chromatography Methods 0.000 description 9
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 125000001589 carboacyl group Chemical group 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
- 229920002472 Starch Polymers 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000008107 starch Substances 0.000 description 5
- 235000019698 starch Nutrition 0.000 description 5
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 5
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- 101000851058 Homo sapiens Neutrophil elastase Proteins 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229960005305 adenosine Drugs 0.000 description 4
- 239000000443 aerosol Substances 0.000 description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 102000052502 human ELANE Human genes 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 108050000203 Adenosine receptors Proteins 0.000 description 3
- 102000009346 Adenosine receptors Human genes 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- 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
- C07H19/167—Purine radicals with ribosyl as the saccharide radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P11/02—Nasal agents, e.g. decongestants
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P11/06—Antiasthmatics
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- A61P11/08—Bronchodilators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
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- 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
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- A—HUMAN NECESSITIES
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- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
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- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
-
- 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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- Life Sciences & Earth Sciences (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0003960.2A GB0003960D0 (en) | 2000-02-18 | 2000-02-18 | Purine derivatives |
| PCT/IB2001/000167 WO2001060835A1 (fr) | 2000-02-18 | 2001-02-09 | Derives de purine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20020676A2 true HRP20020676A2 (en) | 2004-12-31 |
Family
ID=9886026
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20020676 HRP20020676A2 (en) | 2000-02-18 | 2002-08-19 | Purine derivatives |
Country Status (39)
| Country | Link |
|---|---|
| US (1) | US6525032B2 (fr) |
| EP (1) | EP1255764B8 (fr) |
| JP (1) | JP2004508284A (fr) |
| KR (1) | KR20030036138A (fr) |
| CN (1) | CN1400975A (fr) |
| AP (1) | AP2002002598A0 (fr) |
| AR (1) | AR027437A1 (fr) |
| AT (1) | ATE325807T1 (fr) |
| AU (1) | AU2001230440A1 (fr) |
| BG (1) | BG106906A (fr) |
| BR (1) | BR0108408A (fr) |
| CA (1) | CA2400619A1 (fr) |
| CO (1) | CO5271668A1 (fr) |
| CR (1) | CR6722A (fr) |
| CZ (1) | CZ20022703A3 (fr) |
| DE (1) | DE60119492T2 (fr) |
| EA (1) | EA004987B1 (fr) |
| EE (1) | EE200200452A (fr) |
| ES (1) | ES2260199T3 (fr) |
| GB (1) | GB0003960D0 (fr) |
| GT (1) | GT200100027A (fr) |
| HN (1) | HN2001000027A (fr) |
| HR (1) | HRP20020676A2 (fr) |
| HU (1) | HUP0301055A2 (fr) |
| IL (1) | IL150543A0 (fr) |
| IS (1) | IS6458A (fr) |
| MA (1) | MA26873A1 (fr) |
| MX (1) | MXPA02008068A (fr) |
| NO (1) | NO20023894L (fr) |
| NZ (1) | NZ519971A (fr) |
| OA (1) | OA12177A (fr) |
| PA (1) | PA8511801A1 (fr) |
| PE (1) | PE20011122A1 (fr) |
| PL (1) | PL357220A1 (fr) |
| SK (1) | SK11692002A3 (fr) |
| SV (1) | SV2002000317A (fr) |
| TN (1) | TNSN01028A1 (fr) |
| WO (1) | WO2001060835A1 (fr) |
| ZA (1) | ZA200206526B (fr) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| GB9913932D0 (en) * | 1999-06-15 | 1999-08-18 | Pfizer Ltd | Purine derivatives |
| US6753322B2 (en) * | 2000-06-06 | 2004-06-22 | Pfizer Inc | 2-aminocarbonyl-9H-purine derivatives |
| US6921753B2 (en) | 2000-06-27 | 2005-07-26 | Pfizer Inc | Purine derivatives |
| GB0022695D0 (en) | 2000-09-15 | 2000-11-01 | Pfizer Ltd | Purine Derivatives |
| WO2003029264A2 (fr) * | 2001-10-01 | 2003-04-10 | University Of Virginia Patent Foundation | Analogues de 2-propynyle adenosine presentant une activite agoniste de a2a et compositions en contenant |
| GB0129273D0 (en) * | 2001-12-06 | 2002-01-23 | Pfizer Ltd | Crystalline drug form |
| GB0129270D0 (en) * | 2001-12-06 | 2002-01-23 | Pfizer Ltd | Pharmaceutical combination |
| GB0129397D0 (en) * | 2001-12-07 | 2002-01-30 | Pfizer Ltd | Pharmaceutical combination |
| US7414036B2 (en) | 2002-01-25 | 2008-08-19 | Muscagen Limited | Compounds useful as A3 adenosine receptor agonists |
| AR044519A1 (es) | 2003-05-02 | 2005-09-14 | Novartis Ag | Derivados de piridin-tiazol amina y de pirimidin-tiazol amina |
| GB0401334D0 (en) | 2004-01-21 | 2004-02-25 | Novartis Ag | Organic compounds |
| GB0411056D0 (en) | 2004-05-18 | 2004-06-23 | Novartis Ag | Organic compounds |
| DK1758596T3 (da) * | 2004-05-26 | 2010-07-26 | Inotek Pharmaceuticals Corp | Purinderivater som adenosin-A1-receptoragonister og fremgangsmåder til anvendelse deraf |
| EP1778712B1 (fr) * | 2004-08-02 | 2013-01-30 | University Of Virginia Patent Foundation | Analogues de 2-propynyle adenosine comprenant des groupes 5'-ribose modifies presentant une activite agoniste a2a |
| WO2006028618A1 (fr) * | 2004-08-02 | 2006-03-16 | University Of Virginia Patent Foundation | Analogues d'adenosine de propynyle 2-polycyclique presentant des groupes 5'-ribose modifies presentant une activite agoniste de a2a |
| WO2006023272A1 (fr) * | 2004-08-02 | 2006-03-02 | University Of Virginia Patent Foundation | Analogues de 2-polycyclique propynyle adenosine presentant une activite agoniste de a2a |
| US7863253B2 (en) * | 2004-09-20 | 2011-01-04 | Inotek Pharmaceuticals Corporation | Purine Derivatives and methods of use thereof |
| GT200500281A (es) | 2004-10-22 | 2006-04-24 | Novartis Ag | Compuestos organicos. |
| GB0424284D0 (en) | 2004-11-02 | 2004-12-01 | Novartis Ag | Organic compounds |
| GB0426164D0 (en) | 2004-11-29 | 2004-12-29 | Novartis Ag | Organic compounds |
| GB0500785D0 (en) | 2005-01-14 | 2005-02-23 | Novartis Ag | Organic compounds |
| GB0510390D0 (en) | 2005-05-20 | 2005-06-29 | Novartis Ag | Organic compounds |
| US7910708B2 (en) | 2005-10-21 | 2011-03-22 | Novartis Ag | Anti-IL13 human antibodies |
| CA2627319A1 (fr) * | 2005-11-30 | 2007-06-07 | Prakash Jagtap | Derives de purine et leurs procedes d'utilisation |
| GB0601951D0 (en) | 2006-01-31 | 2006-03-15 | Novartis Ag | Organic compounds |
| WO2007092936A2 (fr) * | 2006-02-08 | 2007-08-16 | University Of Virginia Patent Foundation | Procédé pour traiter des lésions gastriques |
| US8178509B2 (en) | 2006-02-10 | 2012-05-15 | University Of Virginia Patent Foundation | Method to treat sickle cell disease |
| GB0607950D0 (en) | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| KR20080110925A (ko) * | 2006-04-21 | 2008-12-19 | 노파르티스 아게 | 아데노신 ａ２ａ 수용체 효능제로서 사용하기 위한 퓨린 유도체 |
| GB0607951D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| US8188063B2 (en) * | 2006-06-19 | 2012-05-29 | University Of Virginia Patent Foundation | Use of adenosine A2A modulators to treat spinal cord injury |
| EP1889846A1 (fr) | 2006-07-13 | 2008-02-20 | Novartis AG | Dérivés de purine comme agonistes du recepteur A2a |
| EP1903044A1 (fr) | 2006-09-14 | 2008-03-26 | Novartis AG | Derivés de l'adénosine en tant qu' agonistes du récepteur A2A |
| DE602007013441D1 (de) | 2006-09-29 | 2011-05-05 | Novartis Ag | Pyrazolopyrimidine als pi3k-lipidkinasehemmer |
| CA2667962A1 (fr) | 2006-10-30 | 2008-05-08 | Novartis Ag | Composes heterocycliques en tant qu'agents anti-inflammatoires |
| JP2008285478A (ja) * | 2007-04-16 | 2008-11-27 | Santen Pharmaceut Co Ltd | アデノシンａ２ａ受容体アゴニストを有効成分として含有する緑内障治療剤 |
| US8058259B2 (en) * | 2007-12-20 | 2011-11-15 | University Of Virginia Patent Foundation | Substituted 4-{3-[6-amino-9-(3,4-dihydroxy-tetrahydro-furan-2-yl)-9H-purin-2-yl]-prop-2-ynyl}-piperidine-1-carboxylic acid esters as A2AR agonists |
| PL2231642T3 (pl) | 2008-01-11 | 2014-04-30 | Novartis Ag | Pirymidyny jako inhibitory kinazy |
| UA104010C2 (en) * | 2008-12-18 | 2013-12-25 | Эли Лилли Энд Компани | Purine compounds |
| PT2391366E (pt) | 2009-01-29 | 2013-02-05 | Novartis Ag | Benzimidazoles substituídos para o tratamento de astrocitomas |
| US8389526B2 (en) | 2009-08-07 | 2013-03-05 | Novartis Ag | 3-heteroarylmethyl-imidazo[1,2-b]pyridazin-6-yl derivatives |
| EP2464649A1 (fr) | 2009-08-12 | 2012-06-20 | Novartis AG | Composés hydrazone hétérocycliques et leurs utilisations pour traiter le cancer et l'inflammation |
| NZ598220A (en) | 2009-08-17 | 2014-02-28 | Intellikine Llc | Heterocyclic compounds and uses thereof |
| CA2771432A1 (fr) | 2009-08-20 | 2011-02-24 | Novartis Ag | Composes d'oximes heterocycliques |
| SG10201502588UA (en) | 2010-01-11 | 2015-05-28 | Inotek Pharmaceuticals Corp | Combination, kit and method of reducing intraocular pressure |
| MX2012010724A (es) | 2010-03-26 | 2012-11-12 | Inotek Pharmaceuticals Corp | Metodo para reducir la presion intraocular en seres humanos empleando n6-ciclopentiladenosina (cpa), derivados de cpa o profarmacos de los mismos. |
| UY33597A (es) | 2010-09-09 | 2012-04-30 | Irm Llc | Compuestos y composiciones como inhibidores de la trk |
| WO2012034095A1 (fr) | 2010-09-09 | 2012-03-15 | Irm Llc | Composés et compositions comme inhibiteurs de trk |
| JP2014505088A (ja) | 2011-02-10 | 2014-02-27 | ノバルティス アーゲー | Ｃ−ＭＥＴチロシンキナーゼ阻害剤としての［１，２，４］トリアゾロ［４，３−ｂ］ピリダジン化合物 |
| JP5808826B2 (ja) | 2011-02-23 | 2015-11-10 | インテリカイン， エルエルシー | 複素環化合物およびその使用 |
| US9102671B2 (en) | 2011-02-25 | 2015-08-11 | Novartis Ag | Compounds and compositions as TRK inhibitors |
| UY34329A (es) | 2011-09-15 | 2013-04-30 | Novartis Ag | Compuestos de triazolopiridina |
| US9174994B2 (en) | 2011-11-23 | 2015-11-03 | Intellikine, Llc | Enhanced treatment regimens using mTor inhibitors |
| US9278991B2 (en) | 2012-01-26 | 2016-03-08 | Inotek Pharmaceuticals Corporation | Anhydrous polymorphs of [(2R,3S,4R,5R)-5-(6-(cyclopentylamino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)} methyl nitrate and processes of preparation thereof |
| CN104245701A (zh) | 2012-04-03 | 2014-12-24 | 诺华有限公司 | 有酪氨酸激酶抑制剂的组合产品和其应用 |
| CN105188714A (zh) | 2013-03-15 | 2015-12-23 | 伊诺泰克制药公司 | 眼用配制品 |
| EP2968340A4 (fr) | 2013-03-15 | 2016-08-10 | Intellikine Llc | Combinaison d'inhibiteurs de kinase et ses utilisations |
| 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 |
| WO2016011658A1 (fr) | 2014-07-25 | 2016-01-28 | Novartis Ag | Polythérapie |
| US20170216297A1 (en) | 2014-07-28 | 2017-08-03 | Technische Universitaet Dresden | Efficient inhibition of hsp27 |
| KR20170036037A (ko) | 2014-07-31 | 2017-03-31 | 노파르티스 아게 | 조합 요법 |
| TWI758146B (zh) * | 2015-03-13 | 2022-03-11 | 瑞典商杜比國際公司 | 解碼具有增強頻譜帶複製元資料在至少一填充元素中的音訊位元流 |
| 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 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5140015A (en) * | 1990-02-20 | 1992-08-18 | Whitby Research, Inc. | 2-aralkoxy and 2-alkoxy adenosine derivatives as coronary vasodilators and antihypertensive agents |
| US5189027A (en) * | 1990-11-30 | 1993-02-23 | Yamasa Shoyu Kabushiki Kaisha | 2-substituted adenosine derivatives and pharmaceutical compositions for circulatory diseases |
| IT1254915B (it) * | 1992-04-24 | 1995-10-11 | Gloria Cristalli | Derivati di adenosina ad attivita' a2 agonista |
| BR9914526A (pt) * | 1998-10-16 | 2001-07-03 | Pfizer | Derivados de adenina |
| GB9913932D0 (en) | 1999-06-15 | 1999-08-18 | Pfizer Ltd | Purine derivatives |
| GB9924361D0 (en) | 1999-10-14 | 1999-12-15 | Pfizer Ltd | Purine derivatives |
| GB9924363D0 (en) | 1999-10-14 | 1999-12-15 | Pfizer Central Res | Purine derivatives |
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2000
- 2000-02-18 GB GBGB0003960.2A patent/GB0003960D0/en not_active Ceased
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2001
- 2001-02-09 NZ NZ519971A patent/NZ519971A/en unknown
- 2001-02-09 KR KR1020027010481A patent/KR20030036138A/ko active IP Right Grant
- 2001-02-09 EA EA200200770A patent/EA004987B1/ru not_active IP Right Cessation
- 2001-02-09 EE EEP200200452A patent/EE200200452A/xx unknown
- 2001-02-09 AP APAP/P/2002/002598A patent/AP2002002598A0/en unknown
- 2001-02-09 HU HU0301055A patent/HUP0301055A2/hu unknown
- 2001-02-09 SK SK1169-2002A patent/SK11692002A3/sk unknown
- 2001-02-09 ES ES01902583T patent/ES2260199T3/es not_active Expired - Lifetime
- 2001-02-09 IL IL15054301A patent/IL150543A0/xx unknown
- 2001-02-09 PL PL01357220A patent/PL357220A1/xx not_active Application Discontinuation
- 2001-02-09 AT AT01902583T patent/ATE325807T1/de not_active IP Right Cessation
- 2001-02-09 DE DE60119492T patent/DE60119492T2/de not_active Expired - Fee Related
- 2001-02-09 OA OA1200200250A patent/OA12177A/en unknown
- 2001-02-09 MX MXPA02008068A patent/MXPA02008068A/es active IP Right Grant
- 2001-02-09 AU AU2001230440A patent/AU2001230440A1/en not_active Abandoned
- 2001-02-09 CZ CZ20022703A patent/CZ20022703A3/cs unknown
- 2001-02-09 CA CA002400619A patent/CA2400619A1/fr not_active Abandoned
- 2001-02-09 WO PCT/IB2001/000167 patent/WO2001060835A1/fr active IP Right Grant
- 2001-02-09 BR BR0108408-9A patent/BR0108408A/pt not_active IP Right Cessation
- 2001-02-09 EP EP01902583A patent/EP1255764B8/fr not_active Expired - Lifetime
- 2001-02-09 JP JP2001560219A patent/JP2004508284A/ja active Pending
- 2001-02-09 CN CN01805069A patent/CN1400975A/zh active Pending
- 2001-02-12 GT GT200100027A patent/GT200100027A/es unknown
- 2001-02-15 CO CO01012091A patent/CO5271668A1/es not_active Application Discontinuation
- 2001-02-15 AR ARP010100690A patent/AR027437A1/es not_active Application Discontinuation
- 2001-02-15 PA PA20018511801A patent/PA8511801A1/es unknown
- 2001-02-15 HN HN2001000027A patent/HN2001000027A/es unknown
- 2001-02-16 TN TNTNSN01028A patent/TNSN01028A1/fr unknown
- 2001-02-16 PE PE2001000174A patent/PE20011122A1/es not_active Application Discontinuation
- 2001-02-16 SV SV2001000317A patent/SV2002000317A/es not_active Application Discontinuation
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2002
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- 2002-08-12 MA MA26771A patent/MA26873A1/fr unknown
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- 2002-08-16 NO NO20023894A patent/NO20023894L/no not_active Application Discontinuation
- 2002-08-19 HR HRP20020676 patent/HRP20020676A2/hr not_active Application Discontinuation
Also Published As
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