SK1352002A3 - 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 PDF

Info

Publication number: SK1352002A3
Authority: SK; Slovakia
Prior art keywords: triazolo; purin; dihydro; preparation; sulfonyl
Prior art date: 1999-07-27

Application number

SK135-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Ferrer Jordi Gracia

Gras Joan Feixas

Soto Jose Manuel Prieto

Noverola Armando Vega

Juan Bernat Vidal

Original Assignee

Almirall Prodesfarma Sa

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.)

1999-07-27

Filing date

2000-07-24

Publication date

2003-04-01

2000-07-24 Application filed by Almirall Prodesfarma Sa filed Critical Almirall Prodesfarma Sa

2003-04-01 Publication of SK1352002A3 publication Critical patent/SK1352002A3/sk

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 15
238000002360 preparation method Methods 0.000 claims abstract description 225
238000000034 method Methods 0.000 claims abstract description 138
150000003839 salts Chemical class 0.000 claims abstract description 18
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
-1 hydroxy, phenyl Chemical group 0.000 claims description 245
150000001875 compounds Chemical class 0.000 claims description 213
229910052739 hydrogen Inorganic materials 0.000 claims description 72
239000000203 mixture Substances 0.000 claims description 53
125000005843 halogen group Chemical group 0.000 claims description 35
125000000217 alkyl group Chemical group 0.000 claims description 31
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
125000004663 dialkyl amino group Chemical group 0.000 claims description 26
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 24
229910052757 nitrogen Inorganic materials 0.000 claims description 23
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 21
125000003545 alkoxy group Chemical group 0.000 claims description 20
239000001257 hydrogen Substances 0.000 claims description 19
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 17
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
238000006243 chemical reaction Methods 0.000 claims description 16
239000002904 solvent Substances 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
125000004076 pyridyl group Chemical group 0.000 claims description 13
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 12
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 12
125000000753 cycloalkyl group Chemical group 0.000 claims description 11
125000002757 morpholinyl group Chemical group 0.000 claims description 11
125000004193 piperazinyl group Chemical group 0.000 claims description 11
125000001424 substituent group Chemical group 0.000 claims description 11
239000004480 active ingredient Substances 0.000 claims description 10
150000001412 amines Chemical class 0.000 claims description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 8
229910052760 oxygen Inorganic materials 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
125000004544 purin-8-yl group Chemical group N1=CN=C2N=C(NC2=C1)* 0.000 claims description 8
229910052717 sulfur Chemical group 0.000 claims description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
125000003342 alkenyl 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
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
125000005842 heteroatom Chemical group 0.000 claims description 7
125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 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
239000001301 oxygen Chemical group 0.000 claims description 7
239000011593 sulfur Chemical group 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 6
125000004414 alkyl thio group Chemical group 0.000 claims description 6
125000002947 alkylene group 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
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
208000037265 diseases, disorders, signs and symptoms Diseases 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
125000002393 azetidinyl group Chemical group 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 5
125000003831 tetrazolyl group Chemical group 0.000 claims description 5
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 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
239000003880 polar aprotic solvent Substances 0.000 claims description 4
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 3
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 3
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 3
LVHGHSDIOOCZLV-UHFFFAOYSA-N 8-[5-(4-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)CC1 LVHGHSDIOOCZLV-UHFFFAOYSA-N 0.000 claims description 3
XHPAHMXVYMVBKD-UHFFFAOYSA-N 8-[5-[3-[(dimethylamino)methyl]azetidin-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)N1CC(CN(C)C)C1 XHPAHMXVYMVBKD-UHFFFAOYSA-N 0.000 claims description 3
JVPTWAWXYMVQTN-UHFFFAOYSA-N 8-[5-[4-(1-hydroxy-2-methylpropan-2-yl)piperazin-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(C)(C)CO)CC1 JVPTWAWXYMVQTN-UHFFFAOYSA-N 0.000 claims description 3
DMCSIHDATSBBBB-UHFFFAOYSA-N 8-[5-[4-(2-hydroxyethyl)piperazin-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(CCO)CC1 DMCSIHDATSBBBB-UHFFFAOYSA-N 0.000 claims description 3
206010007559 Cardiac failure congestive Diseases 0.000 claims description 3
208000010412 Glaucoma Diseases 0.000 claims description 3
206010019280 Heart failures Diseases 0.000 claims description 3
206010020772 Hypertension Diseases 0.000 claims description 3
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 3
208000006673 asthma Diseases 0.000 claims description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
125000003226 pyrazolyl group Chemical group 0.000 claims description 3
125000001425 triazolyl group Chemical group 0.000 claims description 3
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 2
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
YASBDOOWVPJXKK-UHFFFAOYSA-N 6-butyl-8-[5-[4-(2-hydroxyethyl)piperazin-1-yl]sulfonyl-2-propoxyphenyl]-9H-[1,2,4]triazolo[3,4-f]purin-5-one Chemical compound N1C=2C3=NN=CN3C(=O)N(CCCC)C=2N=C1C(C(=CC=1)OCCC)=CC=1S(=O)(=O)N1CCN(CCO)CC1 YASBDOOWVPJXKK-UHFFFAOYSA-N 0.000 claims description 2
206010002388 Angina unstable Diseases 0.000 claims description 2
201000001320 Atherosclerosis Diseases 0.000 claims description 2
101100296726 Caenorhabditis elegans pde-5 gene Proteins 0.000 claims description 2
208000010228 Erectile Dysfunction Diseases 0.000 claims description 2
201000001068 Prinzmetal angina Diseases 0.000 claims description 2
208000001647 Renal Insufficiency Diseases 0.000 claims description 2
206010039085 Rhinitis allergic Diseases 0.000 claims description 2
208000007718 Stable Angina Diseases 0.000 claims description 2
208000006011 Stroke Diseases 0.000 claims description 2
208000007814 Unstable Angina Diseases 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
201000010105 allergic rhinitis Diseases 0.000 claims description 2
210000004204 blood vessel Anatomy 0.000 claims description 2
206010006451 bronchitis Diseases 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
208000023819 chronic asthma Diseases 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
201000001881 impotence Diseases 0.000 claims description 2
230000005764 inhibitory process Effects 0.000 claims description 2
201000004332 intermediate coronary syndrome Diseases 0.000 claims description 2
230000008991 intestinal motility 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
201000006370 kidney failure Diseases 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000005188 oxoalkyl group Chemical group 0.000 claims description 2
230000002093 peripheral effect Effects 0.000 claims description 2
208000002815 pulmonary hypertension Diseases 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
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
208000019553 vascular disease Diseases 0.000 claims description 2
230000004218 vascular function Effects 0.000 claims description 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
DAIWAGVXWYYFCH-IYBDPMFKSA-N 8-[5-[(3R,5S)-3,5-dimethylpiperazin-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)N1C[C@H](C)N[C@H](C)C1 DAIWAGVXWYYFCH-IYBDPMFKSA-N 0.000 claims 1
206010057671 Female sexual dysfunction Diseases 0.000 claims 1
239000000654 additive Substances 0.000 claims 1
230000000996 additive effect Effects 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
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 1
SXYATQLMZOZEFK-UHFFFAOYSA-N n-pyridin-4-ylbenzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC1=CC=NC=C1 SXYATQLMZOZEFK-UHFFFAOYSA-N 0.000 claims 1
208000015891 sexual disease Diseases 0.000 claims 1
229940123333 Phosphodiesterase 5 inhibitor Drugs 0.000 abstract 1
239000002590 phosphodiesterase V inhibitor Substances 0.000 abstract 1
239000007787 solid Substances 0.000 description 166
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 104
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 32
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 11
WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
238000010992 reflux Methods 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 8
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
XCAYUNJSPOEITF-UHFFFAOYSA-N n-[(3-methoxyphenyl)methyl]-1-phenylmethanamine Chemical compound COC1=CC=CC(CNCC=2C=CC=CC=2)=C1 XCAYUNJSPOEITF-UHFFFAOYSA-N 0.000 description 8
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 7
UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 7
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 7
102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 7
108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 7
235000019253 formic acid Nutrition 0.000 description 7
230000014759 maintenance of location Effects 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
239000003826 tablet Substances 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 6
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 6
RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 6
WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 description 5
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 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
QQIGVEZQFKUIJQ-UHFFFAOYSA-N [1,2,4]triazolo[3,4-f]purin-5-one Chemical compound O=C1N=C2N=CN=C2C2=NN=CN12 QQIGVEZQFKUIJQ-UHFFFAOYSA-N 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
239000002585 base Substances 0.000 description 5
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238000002347 injection Methods 0.000 description 5
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FLNQAPQQAZVRDA-UHFFFAOYSA-N 1-(2-(2-Hydroxyethoxy)ethyl)piperazine Chemical compound OCCOCCN1CCNCC1 FLNQAPQQAZVRDA-UHFFFAOYSA-N 0.000 description 4
OBWROQGNIMBKKV-UHFFFAOYSA-N 5,6-diamino-1-butylpyrimidine-2,4-dione Chemical compound CCCCN1C(N)=C(N)C(=O)NC1=O OBWROQGNIMBKKV-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
FVFQMSDZBVTBFU-UHFFFAOYSA-N N-[(4-hydroxy-1-methylpiperidin-4-yl)methyl]-N-methyl-3-(5-oxo-6-propyl-9H-[1,2,4]triazolo[3,4-f]purin-8-yl)-4-propoxybenzenesulfonamide Chemical compound C1=C(C=2NC=3C4=NN=CN4C(=O)N(CCC)C=3N=2)C(OCCC)=CC=C1S(=O)(=O)N(C)CC1(O)CCN(C)CC1 FVFQMSDZBVTBFU-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000002775 capsule Substances 0.000 description 4
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239000003960 organic solvent Substances 0.000 description 4
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CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 4
HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
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230000001681 protective effect Effects 0.000 description 1
UFZNZKGKBWOSJG-UHFFFAOYSA-N purin-2-one Chemical compound O=C1N=CC2=NC=NC2=N1 UFZNZKGKBWOSJG-UHFFFAOYSA-N 0.000 description 1
150000003212 purines Chemical class 0.000 description 1
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
206010037844 rash Diseases 0.000 description 1
239000012048 reactive intermediate Substances 0.000 description 1
229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 1
150000003872 salicylic acid derivatives Chemical class 0.000 description 1
230000036299 sexual function Effects 0.000 description 1
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
229940045902 sodium stearyl fumarate Drugs 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000006190 sub-lingual tablet Substances 0.000 description 1
125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
239000007939 sustained release tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
UXAWXZDXVOYLII-UHFFFAOYSA-N tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C1C2N(C(=O)OC(C)(C)C)CC1NC2 UXAWXZDXVOYLII-UHFFFAOYSA-N 0.000 description 1
GFXFBNWRROYZMV-UHFFFAOYSA-N tert-butyl 5-[2-(oxan-2-yloxy)ethyl]-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC2CC1CN2CCOC1CCCCO1 GFXFBNWRROYZMV-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
239000003643 water by type 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)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Pulmonology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (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)

SK135-2002A 1999-07-27 2000-07-24 8-Phenyl-6,9-dihydro-[1,2,4]triazolo[3,4-i]purin-5-one derivatives SK1352002A3 (en)

Applications Claiming Priority (2)

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.
PCT/EP2000/007062 WO2001007441A1 (en)	1999-07-27	2000-07-24	8-PHENYL-6,9-DIHYDRO-[1,2,4]TRIAZOLO[3,4-i]PURIN-5-ONE DERIVATIVES

Publications (1)

Publication Number	Publication Date
SK1352002A3 true SK1352002A3 (en)	2003-04-01

Family

ID=8309393

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK135-2002A SK1352002A3 (en)	1999-07-27	2000-07-24	8-Phenyl-6,9-dihydro-[1,2,4]triazolo[3,4-i]purin-5-one derivatives

Country Status (34)

Country	Link
US (1)	US7034016B2 (es)
EP (1)	EP1198464B1 (es)
JP (1)	JP2003505461A (es)
KR (1)	KR20020022786A (es)
CN (1)	CN1198825C (es)
AR (1)	AR024969A1 (es)
AT (1)	ATE251625T1 (es)
AU (1)	AU777571B2 (es)
BG (1)	BG106346A (es)
BR (1)	BR0012764A (es)
CA (1)	CA2380181A1 (es)
CO (1)	CO5190717A1 (es)
CZ (1)	CZ2002311A3 (es)
DE (1)	DE60005838T2 (es)
DK (1)	DK1198464T3 (es)
EE (1)	EE200200046A (es)
ES (2)	ES2166270B1 (es)
HK (1)	HK1044332B (es)
HU (1)	HUP0202103A3 (es)
IL (1)	IL147770A0 (es)
MY (1)	MY129590A (es)
NO (1)	NO20020391L (es)
NZ (1)	NZ516780A (es)
PE (1)	PE20010401A1 (es)
PL (1)	PL353827A1 (es)
PT (1)	PT1198464E (es)
RU (1)	RU2258705C2 (es)
SK (1)	SK1352002A3 (es)
TR (1)	TR200200785T2 (es)
TW (1)	TW568912B (es)
UA (1)	UA73513C2 (es)
UY (1)	UY26258A1 (es)
WO (1)	WO2001007441A1 (es)
ZA (1)	ZA200200561B (es)

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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
PE20080251A1 (es)	2006-05-04	2008-04-25	Boehringer Ingelheim Int	Usos de inhibidores de dpp iv
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AR071175A1 (es)	2008-04-03	2010-06-02	Boehringer Ingelheim Int	Composicion farmaceutica que comprende un inhibidor de la dipeptidil-peptidasa-4 (dpp4) y un farmaco acompanante
KR20190016601A (ko)	2008-08-06	2019-02-18	베링거 인겔하임 인터내셔날 게엠베하	메트포르민 요법이 부적합한 환자에서의 당뇨병 치료
UY32030A (es)	2008-08-06	2010-03-26	Boehringer Ingelheim Int	"tratamiento para diabetes en pacientes inapropiados para terapia con metformina"
KR20110067096A (ko)	2008-09-10	2011-06-21	베링거 인겔하임 인터내셔날 게엠베하	당뇨병 및 관련 상태를 치료하기 위한 병용 요법
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
EA022310B1 (ru)	2008-12-23	2015-12-30	Бёрингер Ингельхайм Интернациональ Гмбх	Солевые формы органического соединения
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
BR112012012641A2 (pt)	2009-11-27	2020-08-11	Boehringer Ingelheim International Gmbh	TRATAMENTO DE PACIENTES DIABÉTICOS GENOTIPADOS COM INIBIDORES DE DPP-lVTAL COMO LINAGLIPTINA
KR101927068B1 (ko)	2010-05-05	2018-12-10	베링거 인겔하임 인터내셔날 게엠베하	체중 감소 치료에 후속하는 dpp-4 억제제에 의한 순차적 병용 요법
CA2803504C (en)	2010-06-24	2022-08-30	Boehringer Ingelheim International Gmbh	A combination for diabetes therapy comprising linagliptin and a long-acting insulin
US9034883B2 (en)	2010-11-15	2015-05-19	Boehringer Ingelheim International Gmbh	Vasoprotective and cardioprotective antidiabetic therapy
EP3517539B1 (en)	2011-07-15	2022-12-14	Boehringer Ingelheim International GmbH	Substituted dimeric quinazoline derivative, its preparation and its use in pharmaceutical compositions for the treatment of type i and ii diabetes
US9555001B2 (en)	2012-03-07	2017-01-31	Boehringer Ingelheim International Gmbh	Pharmaceutical composition and uses thereof
EP4151218A1 (en)	2012-05-14	2023-03-22	Boehringer Ingelheim International GmbH	Linagliptin, a xanthine derivative as dpp-4 inhibitor, for use in the treatment of sirs and/or sepsis
JP6224084B2 (ja)	2012-05-14	2017-11-01	ベーリンガーインゲルハイムインターナショナルゲゼルシャフトミットベシュレンクテルハフツング	糸球体上皮細胞関連障害及び／又はネフローゼ症候群の治療に用いるｄｐｐ−４阻害薬としてのキサンチン誘導体
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
CN104583217B (zh)	2012-06-18	2017-11-17	达特神经科学(开曼)有限公司	取代的噻吩稠合的和呋喃稠合的唑并嘧啶‑5‑(6h)‑酮化合物
JP6615109B2 (ja)	2014-02-28	2019-12-04	ベーリンガーインゲルハイムインターナショナルゲゼルシャフトミットベシュレンクテルハフツング	Ｄｐｐ−４阻害薬の医学的使用
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1999
- 1999-07-27 ES ES009901694A patent/ES2166270B1/es not_active Expired - Fee Related
2000
- 2000-07-24 WO PCT/EP2000/007062 patent/WO2001007441A1/en not_active Ceased
- 2000-07-24 UA UA2002010660A patent/UA73513C2/uk unknown
- 2000-07-24 PT PT00949400T patent/PT1198464E/pt unknown
- 2000-07-24 JP JP2001512525A patent/JP2003505461A/ja not_active Withdrawn
- 2000-07-24 EE EEP200200046A patent/EE200200046A/xx unknown
- 2000-07-24 ES ES00949400T patent/ES2208378T3/es not_active Expired - Lifetime
- 2000-07-24 TR TR2002/00785T patent/TR200200785T2/xx unknown
- 2000-07-24 DE DE60005838T patent/DE60005838T2/de not_active Expired - Lifetime
- 2000-07-24 IL IL14777000A patent/IL147770A0/xx unknown
- 2000-07-24 RU RU2002104935/04A patent/RU2258705C2/ru not_active IP Right Cessation
- 2000-07-24 PE PE2000000742A patent/PE20010401A1/es not_active Application Discontinuation
- 2000-07-24 CZ CZ2002311A patent/CZ2002311A3/cs unknown
- 2000-07-24 AU AU62772/00A patent/AU777571B2/en not_active Ceased
- 2000-07-24 NZ NZ516780A patent/NZ516780A/en unknown
- 2000-07-24 PL PL00353827A patent/PL353827A1/xx not_active Application Discontinuation
- 2000-07-24 BR BR0012764-7A patent/BR0012764A/pt not_active IP Right Cessation
- 2000-07-24 HU HU0202103A patent/HUP0202103A3/hu unknown
- 2000-07-24 CN CNB008130760A patent/CN1198825C/zh not_active Expired - Fee Related
- 2000-07-24 AT AT00949400T patent/ATE251625T1/de not_active IP Right Cessation
- 2000-07-24 SK SK135-2002A patent/SK1352002A3/sk unknown
- 2000-07-24 DK DK00949400T patent/DK1198464T3/da active
- 2000-07-24 EP EP00949400A patent/EP1198464B1/en not_active Expired - Lifetime
- 2000-07-24 HK HK02103667.4A patent/HK1044332B/en not_active IP Right Cessation
- 2000-07-24 CA CA002380181A patent/CA2380181A1/en not_active Abandoned
- 2000-07-24 KR KR1020027001155A patent/KR20020022786A/ko not_active Ceased
- 2000-07-26 MY MYPI20003424A patent/MY129590A/en unknown
- 2000-07-26 TW TW089114927A patent/TW568912B/zh active
- 2000-07-26 CO CO00056184A patent/CO5190717A1/es not_active Application Discontinuation
- 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

Also Published As

Publication number	Publication date
CN1374962A (zh)	2002-10-16
KR20020022786A (ko)	2002-03-27
BG106346A (en)	2002-09-30
ES2166270A1 (es)	2002-04-01
HK1044332A1 (en)	2002-10-18
CZ2002311A3 (cs)	2003-01-15
ATE251625T1 (de)	2003-10-15
AU777571B2 (en)	2004-10-21
NO20020391D0 (no)	2002-01-25
PE20010401A1 (es)	2001-04-16
UA73513C2 (en)	2005-08-15
PT1198464E (pt)	2004-02-27
HUP0202103A3 (en)	2004-12-28
US7034016B2 (en)	2006-04-25
IL147770A0 (en)	2002-08-14
ZA200200561B (en)	2003-06-25
RU2258705C2 (ru)	2005-08-20
ES2166270B1 (es)	2003-04-01
MY129590A (en)	2007-04-30
NO20020391L (no)	2002-03-25
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