ZA200200561B - 8-phenyl-6,9-dihydro[1,2,4]triazolo[3,4-i]purin-5-one derivatives. - Google Patents
8-phenyl-6,9-dihydro[1,2,4]triazolo[3,4-i]purin-5-one derivatives. Download PDFInfo
- Publication number
- ZA200200561B ZA200200561B ZA200200561A ZA200200561A ZA200200561B ZA 200200561 B ZA200200561 B ZA 200200561B ZA 200200561 A ZA200200561 A ZA 200200561A ZA 200200561 A ZA200200561 A ZA 200200561A ZA 200200561 B ZA200200561 B ZA 200200561B
- Authority
- ZA
- South Africa
- Prior art keywords
- group
- dihydro
- formula
- compound
- substituted
- Prior art date
Links
- VRWXCYHUNLAQQC-UHFFFAOYSA-N 8-phenyl-6,9-dihydro-[1,2,4]triazolo[3,4-f]purin-5-one Chemical class N1C=2C3=NN=CN3C(=O)NC=2N=C1C1=CC=CC=C1 VRWXCYHUNLAQQC-UHFFFAOYSA-N 0.000 title description 2
- -1 hydroxy, phenyl Chemical group 0.000 claims description 105
- 150000001875 compounds Chemical class 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 125000004193 piperazinyl group Chemical group 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 11
- 125000002757 morpholinyl group Chemical group 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Chemical group 0.000 claims description 8
- 125000005936 piperidyl group Chemical group 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 150000007530 organic bases Chemical class 0.000 claims description 7
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 7
- 125000001425 triazolyl group Chemical group 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 101100296726 Caenorhabditis elegans pde-5 gene Proteins 0.000 claims description 6
- 239000005864 Sulphur Chemical group 0.000 claims description 6
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 6
- HOXPMFBXNMYFSM-UHFFFAOYSA-N 7h-purin-2-ylhydrazine Chemical class NNC1=NC=C2NC=NC2=N1 HOXPMFBXNMYFSM-UHFFFAOYSA-N 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000002393 azetidinyl group Chemical group 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 4
- 208000010228 Erectile Dysfunction Diseases 0.000 claims description 4
- 206010057671 Female sexual dysfunction Diseases 0.000 claims description 4
- 206010019280 Heart failures Diseases 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 4
- 208000006011 Stroke Diseases 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 4
- 201000001881 impotence Diseases 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000003880 polar aprotic solvent Substances 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
- 206010002388 Angina unstable Diseases 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 208000010412 Glaucoma Diseases 0.000 claims description 3
- 208000018262 Peripheral vascular disease Diseases 0.000 claims description 3
- 201000001068 Prinzmetal angina Diseases 0.000 claims description 3
- 208000001647 Renal Insufficiency Diseases 0.000 claims description 3
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 3
- 208000007718 Stable Angina Diseases 0.000 claims description 3
- 208000007814 Unstable Angina Diseases 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 3
- 201000010105 allergic rhinitis Diseases 0.000 claims description 3
- 210000004204 blood vessel Anatomy 0.000 claims description 3
- 206010006451 bronchitis Diseases 0.000 claims description 3
- 208000023819 chronic asthma Diseases 0.000 claims description 3
- 230000010243 gut motility Effects 0.000 claims description 3
- 201000004332 intermediate coronary syndrome Diseases 0.000 claims description 3
- 201000006370 kidney failure Diseases 0.000 claims description 3
- 208000002815 pulmonary hypertension Diseases 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 208000015891 sexual disease Diseases 0.000 claims description 3
- 208000019553 vascular disease Diseases 0.000 claims description 3
- OFQXVHPYWBHEMD-UHFFFAOYSA-N 1-phenyl-3,7-dihydropurine-2,6-dione Chemical compound O=C1NC=2N=CNC=2C(=O)N1C1=CC=CC=C1 OFQXVHPYWBHEMD-UHFFFAOYSA-N 0.000 claims description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 201000009961 allergic asthma Diseases 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 230000005764 inhibitory process Effects 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005188 oxoalkyl group Chemical group 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- DSNYFFJTZPIKFZ-UHFFFAOYSA-N propoxybenzene Chemical group CCCOC1=CC=CC=C1 DSNYFFJTZPIKFZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 2
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 7
- 238000004519 manufacturing process Methods 0.000 claims 5
- 241001465754 Metazoa Species 0.000 claims 2
- NFNGHOHQIANCPW-HNNXBMFYSA-N 8-[5-[(3S)-3-methylpiperazin-1-yl]sulfonyl-2-propoxyphenyl]-6-propyl-9H-[1,2,4]triazolo[3,4-f]purin-5-one Chemical compound C1=C(C=2NC=3C4=NN=CN4C(=O)N(CCC)C=3N=2)C(OCCC)=CC=C1S(=O)(=O)N1CCN[C@@H](C)C1 NFNGHOHQIANCPW-HNNXBMFYSA-N 0.000 claims 1
- 230000000172 allergic effect Effects 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- CNCZCYFROMADJV-UHFFFAOYSA-N purine-6-thione Chemical class S=C1N=CN=C2N=CN=C12 CNCZCYFROMADJV-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 3
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 3
- ACCCXSZCOGNLFL-UHFFFAOYSA-N 8-phenyl-3,7-dihydropurine-2,6-dione Chemical class N1C=2C(=O)NC(=O)NC=2N=C1C1=CC=CC=C1 ACCCXSZCOGNLFL-UHFFFAOYSA-N 0.000 description 3
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 3
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZOOGRGPOEVQQDX-UHFFFAOYSA-N cyclic GMP Natural products O1C2COP(O)(=O)OC2C(O)C1N1C=NC2=C1NC(N)=NC2=O ZOOGRGPOEVQQDX-UHFFFAOYSA-N 0.000 description 3
- 125000002632 imidazolidinyl group Chemical group 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 3
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 3
- 125000002755 pyrazolinyl group Chemical group 0.000 description 3
- 125000000168 pyrrolyl group Chemical group 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-UUOKFMHZSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 2
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 208000002551 irritable bowel syndrome Diseases 0.000 description 2
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 2
- 125000005956 isoquinolyl group Chemical group 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 150000002905 orthoesters Chemical class 0.000 description 2
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 description 1
- SGRODURINDARRU-UHFFFAOYSA-N 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane Chemical compound C1=CC(OC)=CC=C1P1SP(C=2C=CC(OC)=CC=2)S1 SGRODURINDARRU-UHFFFAOYSA-N 0.000 description 1
- QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 101100257262 Caenorhabditis elegans soc-1 gene Proteins 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- MIKUYHXYGGJMLM-GIMIYPNGSA-N Crotonoside Natural products C1=NC2=C(N)NC(=O)N=C2N1[C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O MIKUYHXYGGJMLM-GIMIYPNGSA-N 0.000 description 1
- NYHBQMYGNKIUIF-UHFFFAOYSA-N D-guanosine Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1OC(CO)C(O)C1O NYHBQMYGNKIUIF-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 208000012322 Raynaud phenomenon Diseases 0.000 description 1
- 229940124639 Selective inhibitor Drugs 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 102000011016 Type 5 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 description 1
- 108010037581 Type 5 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000005236 alkanoylamino group Chemical group 0.000 description 1
- 230000003496 anti-amnesic effect Effects 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 230000003182 bronchodilatating effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229940029575 guanosine Drugs 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002633 protecting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 1
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
-
- 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
-
- 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
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- 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
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/22—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one sulfur atom
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pulmonology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Ophthalmology & Optometry (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Vascular Medicine (AREA)
- Immunology (AREA)
- Gynecology & Obstetrics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES009901694A ES2166270B1 (es) | 1999-07-27 | 1999-07-27 | Derivados de 8-fenil-6,9-dihidro-(1,2,4,)triazolo(3,4-i)purin-5-ona. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200200561B true ZA200200561B (en) | 2003-06-25 |
Family
ID=8309393
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200200561A ZA200200561B (en) | 1999-07-27 | 2002-01-22 | 8-phenyl-6,9-dihydro[1,2,4]triazolo[3,4-i]purin-5-one derivatives. |
Country Status (34)
| Country | Link |
|---|---|
| US (1) | US7034016B2 (sk) |
| EP (1) | EP1198464B1 (sk) |
| JP (1) | JP2003505461A (sk) |
| KR (1) | KR20020022786A (sk) |
| CN (1) | CN1198825C (sk) |
| AR (1) | AR024969A1 (sk) |
| AT (1) | ATE251625T1 (sk) |
| AU (1) | AU777571B2 (sk) |
| BG (1) | BG106346A (sk) |
| BR (1) | BR0012764A (sk) |
| CA (1) | CA2380181A1 (sk) |
| CO (1) | CO5190717A1 (sk) |
| CZ (1) | CZ2002311A3 (sk) |
| DE (1) | DE60005838T2 (sk) |
| DK (1) | DK1198464T3 (sk) |
| EE (1) | EE200200046A (sk) |
| ES (2) | ES2166270B1 (sk) |
| HK (1) | HK1044332B (sk) |
| HU (1) | HUP0202103A3 (sk) |
| IL (1) | IL147770A0 (sk) |
| MY (1) | MY129590A (sk) |
| NO (1) | NO20020391L (sk) |
| NZ (1) | NZ516780A (sk) |
| PE (1) | PE20010401A1 (sk) |
| PL (1) | PL353827A1 (sk) |
| PT (1) | PT1198464E (sk) |
| RU (1) | RU2258705C2 (sk) |
| SK (1) | SK1352002A3 (sk) |
| TR (1) | TR200200785T2 (sk) |
| TW (1) | TW568912B (sk) |
| UA (1) | UA73513C2 (sk) |
| UY (1) | UY26258A1 (sk) |
| WO (1) | WO2001007441A1 (sk) |
| ZA (1) | ZA200200561B (sk) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1127506C (zh) | 2001-06-29 | 2003-11-12 | 刘宝顺 | 一种治疗阳痿的新化合物 |
| US7407955B2 (en) | 2002-08-21 | 2008-08-05 | Boehringer Ingelheim Pharma Gmbh & Co., Kg | 8-[3-amino-piperidin-1-yl]-xanthines, the preparation thereof and their use as pharmaceutical compositions |
| SE0300917D0 (sv) | 2003-03-31 | 2003-03-31 | St Jude Medical | Multi-chamber pacing system |
| US20070010450A1 (en) | 2003-06-13 | 2007-01-11 | Microbia, Inc., A Massachusetts Corporation | Methods and compositions for the treatment of gastrointestinal disorders |
| US7501426B2 (en) | 2004-02-18 | 2009-03-10 | Boehringer Ingelheim International Gmbh | 8-[3-amino-piperidin-1-yl]-xanthines, their preparation and their use as pharmaceutical compositions |
| WO2005110983A1 (en) * | 2004-04-29 | 2005-11-24 | Merck & Co., Inc. | Azetidine glycine transporter inhibitors |
| DE102004054054A1 (de) | 2004-11-05 | 2006-05-11 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verfahren zur Herstellung chiraler 8-(3-Amino-piperidin-1-yl)-xanthine |
| US20070037831A1 (en) * | 2004-11-18 | 2007-02-15 | Cynthia Cuffie-Jackson | Methods of using PDE 5 inhibitors for the treatment of congestive heart failure |
| DE102005035891A1 (de) | 2005-07-30 | 2007-02-08 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | 8-(3-Amino-piperidin-1-yl)-xanthine, deren Herstellung und deren Verwendung als Arzneimittel |
| CN102838599A (zh) | 2006-05-04 | 2012-12-26 | 贝林格尔.英格海姆国际有限公司 | 多晶型 |
| EP1852108A1 (en) | 2006-05-04 | 2007-11-07 | Boehringer Ingelheim Pharma GmbH & Co.KG | DPP IV inhibitor formulations |
| PE20080251A1 (es) | 2006-05-04 | 2008-04-25 | Boehringer Ingelheim Int | Usos de inhibidores de dpp iv |
| PE20140960A1 (es) | 2008-04-03 | 2014-08-15 | Boehringer Ingelheim Int | Formulaciones que comprenden un inhibidor de dpp4 |
| UY32030A (es) | 2008-08-06 | 2010-03-26 | Boehringer Ingelheim Int | "tratamiento para diabetes en pacientes inapropiados para terapia con metformina" |
| BRPI0916997A2 (pt) | 2008-08-06 | 2020-12-15 | Boehringer Ingelheim International Gmbh | Inibidor de dpp-4 e seu uso |
| AU2009290911A1 (en) | 2008-09-10 | 2010-03-18 | Boehringer Ingelheim International Gmbh | Combination therapy for the treatment of diabetes and related conditions |
| US20200155558A1 (en) | 2018-11-20 | 2020-05-21 | Boehringer Ingelheim International Gmbh | Treatment for diabetes in patients with insufficient glycemic control despite therapy with an oral antidiabetic drug |
| AU2009331471B2 (en) | 2008-12-23 | 2015-09-03 | Boehringer Ingelheim International Gmbh | Salt forms of organic compound |
| AR074990A1 (es) | 2009-01-07 | 2011-03-02 | Boehringer Ingelheim Int | Tratamiento de diabetes en pacientes con un control glucemico inadecuado a pesar de la terapia con metformina |
| KR102668834B1 (ko) | 2009-11-27 | 2024-05-24 | 베링거 인겔하임 인터내셔날 게엠베하 | 리나글립틴과 같은 ｄｐｐ－ｉｖ 억제제를 사용한 유전자형 검사된 당뇨병 환자의 치료 |
| ES2935300T3 (es) | 2010-05-05 | 2023-03-03 | Boehringer Ingelheim Int | Combiterapia |
| KR20230051307A (ko) | 2010-06-24 | 2023-04-17 | 베링거 인겔하임 인터내셔날 게엠베하 | 당뇨병 요법 |
| US9034883B2 (en) | 2010-11-15 | 2015-05-19 | Boehringer Ingelheim International Gmbh | Vasoprotective and cardioprotective antidiabetic therapy |
| EA030121B1 (ru) | 2011-07-15 | 2018-06-29 | Бёрингер Ингельхайм Интернациональ Гмбх | Замещенные хиназолины, их получение и их применение в фармацевтических композициях |
| US9555001B2 (en) | 2012-03-07 | 2017-01-31 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition and uses thereof |
| WO2013171167A1 (en) | 2012-05-14 | 2013-11-21 | Boehringer Ingelheim International Gmbh | A xanthine derivative as dpp -4 inhibitor for use in the treatment of podocytes related disorders and/or nephrotic syndrome |
| WO2013174767A1 (en) | 2012-05-24 | 2013-11-28 | Boehringer Ingelheim International Gmbh | A xanthine derivative as dpp -4 inhibitor for use in modifying food intake and regulating food preference |
| RU2653054C2 (ru) | 2012-06-18 | 2018-05-07 | Дарт Нейросайенс (Кайман) Лтд | Замещенные соединения пиридин азолопиримидин-5-(6н)-она |
| ES2950384T3 (es) | 2014-02-28 | 2023-10-09 | Boehringer Ingelheim Int | Uso médico de un inhibidor de DPP-4 |
| EP4233840A3 (en) | 2016-06-10 | 2023-10-18 | Boehringer Ingelheim International GmbH | Combinations of linagliptin and metformin |
| CA3087655A1 (en) | 2018-01-04 | 2019-07-11 | Impetis Biosciences Ltd. | Tricyclic compounds, compositions and medicinal applications thereof |
| TWI837171B (zh) * | 2018-08-30 | 2024-04-01 | 日商鐵勒史東股份有限公司 | 用於抑制黃嘌呤氧化酶之肼基嘌呤化合物及三唑嘌呤化合物 |
| CN112225761B (zh) * | 2020-12-16 | 2021-03-12 | 南京颐媛生物医学研究院有限公司 | 一种嘧啶并三氮唑及其合成方法 |
| EP4305033A1 (en) * | 2021-03-09 | 2024-01-17 | Basf Se | Tricyclic pesticidal compounds |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4593095A (en) * | 1983-02-18 | 1986-06-03 | The Johns Hopkins University | Xanthine derivatives |
| DE3347290A1 (de) * | 1983-12-28 | 1985-07-11 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue 2-phenyl-imidazole, ihre herstellung und diese verbindungen enthaltende arzneimittel |
| EP0417790B1 (en) * | 1989-09-14 | 1996-12-04 | Kyowa Hakko Kogyo Co., Ltd. | S-triazolo[3,4-i]purine derivatives |
| GB9013750D0 (en) * | 1990-06-20 | 1990-08-08 | Pfizer Ltd | Therapeutic agents |
| EP0811624A1 (en) * | 1995-02-21 | 1997-12-10 | Yamasa Corporation | Purine compounds and xanthine oxidase inhibitors |
| EP0977756A1 (en) * | 1997-04-25 | 2000-02-09 | Pfizer Limited | PYRAZOLOPYRIMIDINONES WHICH INHIBIT TYPE 5 CYCLIC GUANOSINE 3',5'-MONOPHOSPHATE PHOSPHODIESTERASE (cGMP PDE5) FOR THE TREATMENT OF SEXUAL DYSFUNCTION |
| WO1999062905A1 (en) * | 1998-06-03 | 1999-12-09 | Almirall Prodesfarma, S.A. | 8-phenylxanthine derivatives and their use as phosphodiesterase inhibitors |
| AU2001289782A1 (en) * | 2000-08-09 | 2002-02-18 | Almirall Prodesfarma, S.A. | Pyrrolotriazolopyrimidinone derivatives |
-
1999
- 1999-07-27 ES ES009901694A patent/ES2166270B1/es not_active Expired - Fee Related
-
2000
- 2000-07-24 TR TR2002/00785T patent/TR200200785T2/xx unknown
- 2000-07-24 NZ NZ516780A patent/NZ516780A/en unknown
- 2000-07-24 PE PE2000000742A patent/PE20010401A1/es not_active Application Discontinuation
- 2000-07-24 AU AU62772/00A patent/AU777571B2/en not_active Ceased
- 2000-07-24 DK DK00949400T patent/DK1198464T3/da active
- 2000-07-24 RU RU2002104935/04A patent/RU2258705C2/ru not_active IP Right Cessation
- 2000-07-24 CN CNB008130760A patent/CN1198825C/zh not_active Expired - Fee Related
- 2000-07-24 PL PL00353827A patent/PL353827A1/xx not_active Application Discontinuation
- 2000-07-24 IL IL14777000A patent/IL147770A0/xx unknown
- 2000-07-24 UA UA2002010660A patent/UA73513C2/uk unknown
- 2000-07-24 BR BR0012764-7A patent/BR0012764A/pt not_active IP Right Cessation
- 2000-07-24 SK SK135-2002A patent/SK1352002A3/sk unknown
- 2000-07-24 AT AT00949400T patent/ATE251625T1/de not_active IP Right Cessation
- 2000-07-24 KR KR1020027001155A patent/KR20020022786A/ko not_active Application Discontinuation
- 2000-07-24 PT PT00949400T patent/PT1198464E/pt unknown
- 2000-07-24 ES ES00949400T patent/ES2208378T3/es not_active Expired - Lifetime
- 2000-07-24 CA CA002380181A patent/CA2380181A1/en not_active Abandoned
- 2000-07-24 EE EEP200200046A patent/EE200200046A/xx unknown
- 2000-07-24 JP JP2001512525A patent/JP2003505461A/ja not_active Withdrawn
- 2000-07-24 HU HU0202103A patent/HUP0202103A3/hu unknown
- 2000-07-24 DE DE60005838T patent/DE60005838T2/de not_active Expired - Lifetime
- 2000-07-24 EP EP00949400A patent/EP1198464B1/en not_active Expired - Lifetime
- 2000-07-24 CZ CZ2002311A patent/CZ2002311A3/cs unknown
- 2000-07-24 WO PCT/EP2000/007062 patent/WO2001007441A1/en active IP Right Grant
- 2000-07-26 CO CO00056184A patent/CO5190717A1/es not_active Application Discontinuation
- 2000-07-26 MY MYPI20003424A patent/MY129590A/en unknown
- 2000-07-26 TW TW089114927A patent/TW568912B/zh active
- 2000-07-27 UY UY26258A patent/UY26258A1/es not_active Application Discontinuation
- 2000-07-27 AR ARP000103896A patent/AR024969A1/es not_active Application Discontinuation
-
2002
- 2002-01-22 ZA ZA200200561A patent/ZA200200561B/en unknown
- 2002-01-24 BG BG06346A patent/BG106346A/xx unknown
- 2002-01-25 NO NO20020391A patent/NO20020391L/no unknown
- 2002-01-25 US US10/057,847 patent/US7034016B2/en not_active Expired - Fee Related
- 2002-05-15 HK HK02103667.4A patent/HK1044332B/zh not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ZA200200561B (en) | 8-phenyl-6,9-dihydro[1,2,4]triazolo[3,4-i]purin-5-one derivatives. | |
| AU2002225096B2 (en) | Cyclin-dependent kinase (CDK) and glycogen synthase kinase-3 (GSK-3) inhibitors | |
| EP1286997B1 (en) | 6-phenylpyrrolopyrimidinedione derivatives | |
| AU781028B2 (en) | Imidazo (1,3,5) triazinones and the use thereof | |
| SG189706A1 (en) | 1-heterocyclyl-1,5-dihydro-pyrazolo[3,4-d] pyrimidin-4-one derivatives and their use as pde9a modulators | |
| JP2012532152A (ja) | Ｊａｋ受容体およびタンパク質チロシンキナーゼ阻害薬としての複素環化合物 | |
| AU2012217208A1 (en) | 6 - cyclobutyl - 1, 5 - dihydro - pyrazolo [3, 4-d] pyrimidin- 4 - one derivatives their use as PDE9A inhibitors | |
| EP1633756B1 (en) | A2a adenosine receptor antagonists | |
| PT2017278T (pt) | Derivado de dihidropirazolopirimidinona | |
| AU2009276420A1 (en) | Piperidine derivatives as JAK3 inhibitors | |
| ES2208063B1 (es) | Nuevos derivados de la 4-(pirrolopirimidin-6-il)bencenosulfonamida. | |
| WO1999062905A1 (en) | 8-phenylxanthine derivatives and their use as phosphodiesterase inhibitors | |
| AU2024200431A1 (en) | Pyrimidine-Based Bicycles as Antiviral Agents for the Treatment and Prevention of HIV Infection | |
| EP1307458B1 (en) | Pyrrolotriazolopyrimidinone derivatives | |
| MXPA02000908A (en) | 8-PHENYL-6,9-DIHYDRO-[1,2,4]TRIAZOLO[3,4-i | |
| JPWO2004096812A1 (ja) | 縮合ピリミジン誘導体 |