RU2006107579A - 6-[(замещенный)фенил]триазолопиримидины в качестве противораковых препаратов - Google Patents
6-[(замещенный)фенил]триазолопиримидины в качестве противораковых препаратов Download PDFInfo
- Publication number
- RU2006107579A RU2006107579A RU2006107579/04A RU2006107579A RU2006107579A RU 2006107579 A RU2006107579 A RU 2006107579A RU 2006107579/04 A RU2006107579/04 A RU 2006107579/04A RU 2006107579 A RU2006107579 A RU 2006107579A RU 2006107579 A RU2006107579 A RU 2006107579A
- Authority
- RU
- Russia
- Prior art keywords
- triazolo
- chloro
- trifluoro
- methylethyl
- pyrimidin
- Prior art date
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- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 title 1
- 239000002246 antineoplastic agent Substances 0.000 title 1
- 229940041181 antineoplastic drug Drugs 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims 88
- 150000001875 compounds Chemical class 0.000 claims 28
- 238000000034 method Methods 0.000 claims 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 11
- 125000004429 atom Chemical group 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 8
- QOXCEADXSTZKHA-UHFFFAOYSA-N [1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound NC1=CC=NC2=NC=NN12 QOXCEADXSTZKHA-UHFFFAOYSA-N 0.000 claims 7
- 239000002585 base Substances 0.000 claims 7
- 229910052794 bromium Inorganic materials 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 229910052801 chlorine Inorganic materials 0.000 claims 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 6
- 241000124008 Mammalia Species 0.000 claims 5
- 102000004243 Tubulin Human genes 0.000 claims 5
- 108090000704 Tubulin Proteins 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- TUXZQBYIZLWUKK-AFIAKLHKSA-N (e)-but-2-enedioic acid;5-chloro-6-[2,6-difluoro-4-[3-(methylamino)propoxy]phenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound OC(=O)\C=C\C(O)=O.FC1=CC(OCCCNC)=CC(F)=C1C1=C(N[C@@H](C)C(F)(F)F)N2N=CN=C2N=C1Cl TUXZQBYIZLWUKK-AFIAKLHKSA-N 0.000 claims 4
- -1 5-chloro-7 - {[(1S) -2,2,2-trifluoro-1-methylethyl] amino} [1,2,4] -triazolo- [1,5-a] pyrimidin-6-yl Chemical group 0.000 claims 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 4
- 150000001412 amines Chemical class 0.000 claims 4
- OVAKAPOZRCLUHN-FVGYRXGTSA-N butanedioic acid;5-chloro-6-[2,6-difluoro-4-[3-(methylamino)propoxy]phenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound OC(=O)CCC(O)=O.FC1=CC(OCCCNC)=CC(F)=C1C1=C(N[C@@H](C)C(F)(F)F)N2N=CN=C2N=C1Cl OVAKAPOZRCLUHN-FVGYRXGTSA-N 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- 239000012634 fragment Substances 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- XFBCIULBTBLLOK-UHFFFAOYSA-N 1-n,1-n-dimethylbutane-1,3-diamine Chemical compound CC(N)CCN(C)C XFBCIULBTBLLOK-UHFFFAOYSA-N 0.000 claims 3
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 3
- ZUZPCOQWSYNWLU-VIFPVBQESA-N 5-chloro-6-[2,6-difluoro-4-[3-(methylamino)propoxy]phenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC(OCCCNC)=CC(F)=C1C1=C(N[C@@H](C)C(F)(F)F)N2N=CN=C2N=C1Cl ZUZPCOQWSYNWLU-VIFPVBQESA-N 0.000 claims 3
- ZSLWBWNJXMEWNY-JTQLQIEISA-N 5-chloro-6-[4-[3-(dimethylamino)propoxy]-2,6-difluorophenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@@H](C)C(F)(F)F)=C1C1=C(F)C=C(OCCCN(C)C)C=C1F ZSLWBWNJXMEWNY-JTQLQIEISA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 239000000010 aprotic solvent Substances 0.000 claims 3
- 230000036457 multidrug resistance Effects 0.000 claims 3
- 239000011593 sulfur Substances 0.000 claims 3
- UUFXQPPJVCARJY-CBVSRFFLSA-N (e)-but-2-enedioic acid;5-chloro-6-[2,6-difluoro-4-[3-(methylamino)propoxy]phenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine;dihydrate Chemical compound O.O.OC(=O)\C=C\C(O)=O.FC1=CC(OCCCNC)=CC(F)=C1C1=C(N[C@@H](C)C(F)(F)F)N2N=CN=C2N=C1Cl UUFXQPPJVCARJY-CBVSRFFLSA-N 0.000 claims 2
- LQUQZWNUVMXWOH-ZETCQYMHSA-N 2-[4-[5-chloro-7-[[(2s)-1,1,1-trifluoropropan-2-yl]amino]-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]-3,5-difluorophenoxy]ethanol Chemical compound ClC1=NC2=NC=NN2C(N[C@@H](C)C(F)(F)F)=C1C1=C(F)C=C(OCCO)C=C1F LQUQZWNUVMXWOH-ZETCQYMHSA-N 0.000 claims 2
- GINJNNGWMNSBIG-UHFFFAOYSA-N 2-n-methylpropane-1,2-diamine Chemical compound CNC(C)CN GINJNNGWMNSBIG-UHFFFAOYSA-N 0.000 claims 2
- PYOBBMDUGURFMC-QMMMGPOBSA-N 3-[4-[5-chloro-7-[[(2s)-1,1,1-trifluoropropan-2-yl]amino]-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]-3,5-difluorophenoxy]propan-1-ol Chemical compound ClC1=NC2=NC=NN2C(N[C@@H](C)C(F)(F)F)=C1C1=C(F)C=C(OCCCO)C=C1F PYOBBMDUGURFMC-QMMMGPOBSA-N 0.000 claims 2
- JTYYWQRSEPVEHP-UHFFFAOYSA-N 3-n-methylbutane-1,3-diamine Chemical compound CNC(C)CCN JTYYWQRSEPVEHP-UHFFFAOYSA-N 0.000 claims 2
- MIZWZYPKIVHIRV-NSHDSACASA-N 5-chloro-6-[2,6-difluoro-4-(2-morpholin-4-ylethoxy)phenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@@H](C)C(F)(F)F)=C1C(C(=C1)F)=C(F)C=C1OCCN1CCOCC1 MIZWZYPKIVHIRV-NSHDSACASA-N 0.000 claims 2
- QKXFUKJAICMMGW-LBPRGKRZSA-N 5-chloro-6-[2,6-difluoro-4-(3-morpholin-4-ylpropoxy)phenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@@H](C)C(F)(F)F)=C1C(C(=C1)F)=C(F)C=C1OCCCN1CCOCC1 QKXFUKJAICMMGW-LBPRGKRZSA-N 0.000 claims 2
- UWVYORNWUVNEHV-ZDUSSCGKSA-N 5-chloro-6-[2,6-difluoro-4-(3-piperidin-1-ylpropoxy)phenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@@H](C)C(F)(F)F)=C1C(C(=C1)F)=C(F)C=C1OCCCN1CCCCC1 UWVYORNWUVNEHV-ZDUSSCGKSA-N 0.000 claims 2
- MEZUNAKNPOIBGG-LBPRGKRZSA-N 5-chloro-6-[2,6-difluoro-4-(3-pyrrolidin-1-ylpropoxy)phenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@@H](C)C(F)(F)F)=C1C(C(=C1)F)=C(F)C=C1OCCCN1CCCC1 MEZUNAKNPOIBGG-LBPRGKRZSA-N 0.000 claims 2
- ZYLQMJCSPMXOHL-QMMMGPOBSA-N 5-chloro-6-[2,6-difluoro-4-[2-(methylamino)ethoxy]phenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC(OCCNC)=CC(F)=C1C1=C(N[C@@H](C)C(F)(F)F)N2N=CN=C2N=C1Cl ZYLQMJCSPMXOHL-QMMMGPOBSA-N 0.000 claims 2
- ZAJCZMAIPRGPFP-ZDUSSCGKSA-N 5-chloro-6-[2,6-difluoro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@@H](C)C(F)(F)F)=C1C(C(=C1)F)=C(F)C=C1OCCCN1CCN(C)CC1 ZAJCZMAIPRGPFP-ZDUSSCGKSA-N 0.000 claims 2
- ZUZPCOQWSYNWLU-SECBINFHSA-N 5-chloro-6-[2,6-difluoro-4-[3-(methylamino)propoxy]phenyl]-n-[(2r)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC(OCCCNC)=CC(F)=C1C1=C(N[C@H](C)C(F)(F)F)N2N=CN=C2N=C1Cl ZUZPCOQWSYNWLU-SECBINFHSA-N 0.000 claims 2
- HAFUDZOLFLXVIY-FVGYRXGTSA-N 5-chloro-6-[2,6-difluoro-4-[3-(methylamino)propoxy]phenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine;hydrochloride Chemical compound Cl.FC1=CC(OCCCNC)=CC(F)=C1C1=C(N[C@@H](C)C(F)(F)F)N2N=CN=C2N=C1Cl HAFUDZOLFLXVIY-FVGYRXGTSA-N 0.000 claims 2
- GXPIFHVEFPCZPS-JTQLQIEISA-N 5-chloro-6-[3-[3-(dimethylamino)propoxy]-2,6-difluorophenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@@H](C)C(F)(F)F)=C1C1=C(F)C=CC(OCCCN(C)C)=C1F GXPIFHVEFPCZPS-JTQLQIEISA-N 0.000 claims 2
- QHBMOSBSGXNWHS-NSHDSACASA-N 5-chloro-6-[3-[4-(dimethylamino)butoxy]-2,6-difluorophenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@@H](C)C(F)(F)F)=C1C1=C(F)C=CC(OCCCCN(C)C)=C1F QHBMOSBSGXNWHS-NSHDSACASA-N 0.000 claims 2
- FDKOUKLCYAUQES-VIFPVBQESA-N 5-chloro-6-[4-[2-(dimethylamino)ethoxy]-2,6-difluorophenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@@H](C)C(F)(F)F)=C1C1=C(F)C=C(OCCN(C)C)C=C1F FDKOUKLCYAUQES-VIFPVBQESA-N 0.000 claims 2
- KUPGUXGPNHKBCS-NSHDSACASA-N 5-chloro-6-[4-[3-(dimethylamino)propoxy]-2-fluorophenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@@H](C)C(F)(F)F)=C1C1=CC=C(OCCCN(C)C)C=C1F KUPGUXGPNHKBCS-NSHDSACASA-N 0.000 claims 2
- YTOAWZMMRBSRKF-JTQLQIEISA-N 5-chloro-6-[4-[3-(ethylamino)propoxy]-2,6-difluorophenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC(OCCCNCC)=CC(F)=C1C1=C(N[C@@H](C)C(F)(F)F)N2N=CN=C2N=C1Cl YTOAWZMMRBSRKF-JTQLQIEISA-N 0.000 claims 2
- CURGABWHJJUZTD-NSHDSACASA-N 5-chloro-6-[4-[3-[ethyl(methyl)amino]propoxy]-2,6-difluorophenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC(OCCCN(C)CC)=CC(F)=C1C1=C(N[C@@H](C)C(F)(F)F)N2N=CN=C2N=C1Cl CURGABWHJJUZTD-NSHDSACASA-N 0.000 claims 2
- SCUBGTBLFXCHHE-NSHDSACASA-N 5-chloro-6-[4-[4-(dimethylamino)butyl]-2,6-difluorophenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@@H](C)C(F)(F)F)=C1C1=C(F)C=C(CCCCN(C)C)C=C1F SCUBGTBLFXCHHE-NSHDSACASA-N 0.000 claims 2
- LZZPXHJWPSSTMF-QMMMGPOBSA-N 6-[4-(3-aminopropoxy)-2,6-difluorophenyl]-5-chloro-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@@H](C)C(F)(F)F)=C1C1=C(F)C=C(OCCCN)C=C1F LZZPXHJWPSSTMF-QMMMGPOBSA-N 0.000 claims 2
- USLPKKDUHYSBFJ-NSHDSACASA-N 6-[4-[3-(azetidin-1-yl)propoxy]-2,6-difluorophenyl]-5-chloro-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@@H](C)C(F)(F)F)=C1C(C(=C1)F)=C(F)C=C1OCCCN1CCC1 USLPKKDUHYSBFJ-NSHDSACASA-N 0.000 claims 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical group CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 2
- 150000008044 alkali metal hydroxides Chemical group 0.000 claims 2
- FWNIBMRSBSSPNP-DXYFNVQQSA-N butanedioic acid;5-chloro-6-[2,6-difluoro-4-[3-(methylamino)propoxy]phenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine;dihydrate Chemical compound O.O.OC(=O)CCC(O)=O.FC1=CC(OCCCNC)=CC(F)=C1C1=C(N[C@@H](C)C(F)(F)F)N2N=CN=C2N=C1Cl FWNIBMRSBSSPNP-DXYFNVQQSA-N 0.000 claims 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 150000005690 diesters Chemical class 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N fumaric acid group Chemical group C(\C=C\C(=O)O)(=O)O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 2
- LQUQZWNUVMXWOH-SSDOTTSWSA-N 2-[4-[5-chloro-7-[[(2r)-1,1,1-trifluoropropan-2-yl]amino]-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]-3,5-difluorophenoxy]ethanol Chemical compound ClC1=NC2=NC=NN2C(N[C@H](C)C(F)(F)F)=C1C1=C(F)C=C(OCCO)C=C1F LQUQZWNUVMXWOH-SSDOTTSWSA-N 0.000 claims 1
- KVOOSXCEKNENEY-UHFFFAOYSA-N 3-[4-(5-chloro-7-cycloheptyl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)-3,5-difluorophenoxy]-n,n-dimethylpropan-1-amine Chemical compound FC1=CC(OCCCN(C)C)=CC(F)=C1C1=C(C2CCCCCC2)N2N=CN=C2N=C1Cl KVOOSXCEKNENEY-UHFFFAOYSA-N 0.000 claims 1
- SILNEJLZHQBBBR-UHFFFAOYSA-N 3-[4-(5-chloro-7-cycloheptyl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)-3,5-difluorophenoxy]propan-1-ol Chemical compound FC1=CC(OCCCO)=CC(F)=C1C1=C(C2CCCCCC2)N2N=CN=C2N=C1Cl SILNEJLZHQBBBR-UHFFFAOYSA-N 0.000 claims 1
- TURWXBQPPKQQIC-UHFFFAOYSA-N 4-[4-(4-oxobutylamino)butylamino]butanal Chemical compound O=CCCCNCCCCNCCCC=O TURWXBQPPKQQIC-UHFFFAOYSA-N 0.000 claims 1
- NSIRLJFAZOCMEI-VIFPVBQESA-N 4-[4-[5-chloro-7-[[(2s)-1,1,1-trifluoropropan-2-yl]amino]-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]-3,5-difluorophenoxy]butan-1-ol Chemical compound ClC1=NC2=NC=NN2C(N[C@@H](C)C(F)(F)F)=C1C1=C(F)C=C(OCCCCO)C=C1F NSIRLJFAZOCMEI-VIFPVBQESA-N 0.000 claims 1
- VFFSFDFJZAYCBT-JTQLQIEISA-N 5-bromo-6-[4-[3-(dimethylamino)propoxy]-2,6-difluorophenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound BrC1=NC2=NC=NN2C(N[C@@H](C)C(F)(F)F)=C1C1=C(F)C=C(OCCCN(C)C)C=C1F VFFSFDFJZAYCBT-JTQLQIEISA-N 0.000 claims 1
- MIZWZYPKIVHIRV-LLVKDONJSA-N 5-chloro-6-[2,6-difluoro-4-(2-morpholin-4-ylethoxy)phenyl]-n-[(2r)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@H](C)C(F)(F)F)=C1C(C(=C1)F)=C(F)C=C1OCCN1CCOCC1 MIZWZYPKIVHIRV-LLVKDONJSA-N 0.000 claims 1
- QKXFUKJAICMMGW-GFCCVEGCSA-N 5-chloro-6-[2,6-difluoro-4-(3-morpholin-4-ylpropoxy)phenyl]-n-[(2r)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@H](C)C(F)(F)F)=C1C(C(=C1)F)=C(F)C=C1OCCCN1CCOCC1 QKXFUKJAICMMGW-GFCCVEGCSA-N 0.000 claims 1
- UWVYORNWUVNEHV-CYBMUJFWSA-N 5-chloro-6-[2,6-difluoro-4-(3-piperidin-1-ylpropoxy)phenyl]-n-[(2r)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@H](C)C(F)(F)F)=C1C(C(=C1)F)=C(F)C=C1OCCCN1CCCCC1 UWVYORNWUVNEHV-CYBMUJFWSA-N 0.000 claims 1
- MEZUNAKNPOIBGG-GFCCVEGCSA-N 5-chloro-6-[2,6-difluoro-4-(3-pyrrolidin-1-ylpropoxy)phenyl]-n-[(2r)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@H](C)C(F)(F)F)=C1C(C(=C1)F)=C(F)C=C1OCCCN1CCCC1 MEZUNAKNPOIBGG-GFCCVEGCSA-N 0.000 claims 1
- ZYLQMJCSPMXOHL-MRVPVSSYSA-N 5-chloro-6-[2,6-difluoro-4-[2-(methylamino)ethoxy]phenyl]-n-[(2r)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC(OCCNC)=CC(F)=C1C1=C(N[C@H](C)C(F)(F)F)N2N=CN=C2N=C1Cl ZYLQMJCSPMXOHL-MRVPVSSYSA-N 0.000 claims 1
- ZAJCZMAIPRGPFP-CYBMUJFWSA-N 5-chloro-6-[2,6-difluoro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-n-[(2r)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@H](C)C(F)(F)F)=C1C(C(=C1)F)=C(F)C=C1OCCCN1CCN(C)CC1 ZAJCZMAIPRGPFP-CYBMUJFWSA-N 0.000 claims 1
- GHMHOHRZRISOHU-UHFFFAOYSA-N 5-chloro-6-[2,6-difluoro-4-[3-(methylamino)propoxy]phenyl]-n-(2,2,2-trifluoroethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC(OCCCNC)=CC(F)=C1C1=C(NCC(F)(F)F)N2N=CN=C2N=C1Cl GHMHOHRZRISOHU-UHFFFAOYSA-N 0.000 claims 1
- JNSFRMDQQFZFBJ-CYBMUJFWSA-N 5-chloro-6-[2,6-difluoro-4-[3-(methylamino)propoxy]phenyl]-n-[(2r)-1,1,1-trifluorobutan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@H](CC)C(F)(F)F)=C1C1=C(F)C=C(OCCCNC)C=C1F JNSFRMDQQFZFBJ-CYBMUJFWSA-N 0.000 claims 1
- XAKKESNRKUXRPK-VIFPVBQESA-N 5-chloro-6-[3-[2-(dimethylamino)ethoxy]-2,6-difluorophenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@@H](C)C(F)(F)F)=C1C1=C(F)C=CC(OCCN(C)C)=C1F XAKKESNRKUXRPK-VIFPVBQESA-N 0.000 claims 1
- FDKOUKLCYAUQES-SECBINFHSA-N 5-chloro-6-[4-[2-(dimethylamino)ethoxy]-2,6-difluorophenyl]-n-[(2r)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@H](C)C(F)(F)F)=C1C1=C(F)C=C(OCCN(C)C)C=C1F FDKOUKLCYAUQES-SECBINFHSA-N 0.000 claims 1
- UYUJACMPNPNLMY-UHFFFAOYSA-N 5-chloro-6-[4-[3-(dimethylamino)propoxy]-2,6-difluorophenyl]-n-(2,2,2-trifluoroethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC(OCCCN(C)C)=CC(F)=C1C1=C(NCC(F)(F)F)N2N=CN=C2N=C1Cl UYUJACMPNPNLMY-UHFFFAOYSA-N 0.000 claims 1
- ZSLWBWNJXMEWNY-SNVBAGLBSA-N 5-chloro-6-[4-[3-(dimethylamino)propoxy]-2,6-difluorophenyl]-n-[(2r)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@H](C)C(F)(F)F)=C1C1=C(F)C=C(OCCCN(C)C)C=C1F ZSLWBWNJXMEWNY-SNVBAGLBSA-N 0.000 claims 1
- KUPGUXGPNHKBCS-LLVKDONJSA-N 5-chloro-6-[4-[3-(dimethylamino)propoxy]-2-fluorophenyl]-n-[(2r)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@H](C)C(F)(F)F)=C1C1=CC=C(OCCCN(C)C)C=C1F KUPGUXGPNHKBCS-LLVKDONJSA-N 0.000 claims 1
- ZRCJRHPNKUDZSW-SNVBAGLBSA-N 5-chloro-6-[4-[3-(dimethylamino)propylsulfanyl]-2,6-difluorophenyl]-n-[(2r)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@H](C)C(F)(F)F)=C1C1=C(F)C=C(SCCCN(C)C)C=C1F ZRCJRHPNKUDZSW-SNVBAGLBSA-N 0.000 claims 1
- ZRCJRHPNKUDZSW-JTQLQIEISA-N 5-chloro-6-[4-[3-(dimethylamino)propylsulfanyl]-2,6-difluorophenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@@H](C)C(F)(F)F)=C1C1=C(F)C=C(SCCCN(C)C)C=C1F ZRCJRHPNKUDZSW-JTQLQIEISA-N 0.000 claims 1
- YTOAWZMMRBSRKF-SNVBAGLBSA-N 5-chloro-6-[4-[3-(ethylamino)propoxy]-2,6-difluorophenyl]-n-[(2r)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC(OCCCNCC)=CC(F)=C1C1=C(N[C@H](C)C(F)(F)F)N2N=CN=C2N=C1Cl YTOAWZMMRBSRKF-SNVBAGLBSA-N 0.000 claims 1
- CURGABWHJJUZTD-LLVKDONJSA-N 5-chloro-6-[4-[3-[ethyl(methyl)amino]propoxy]-2,6-difluorophenyl]-n-[(2r)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC(OCCCN(C)CC)=CC(F)=C1C1=C(N[C@H](C)C(F)(F)F)N2N=CN=C2N=C1Cl CURGABWHJJUZTD-LLVKDONJSA-N 0.000 claims 1
- HAVQJWSGEOOVKZ-LLVKDONJSA-N 5-chloro-6-[4-[4-(dimethylamino)butoxy]-2,6-difluorophenyl]-n-[(2r)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@H](C)C(F)(F)F)=C1C1=C(F)C=C(OCCCCN(C)C)C=C1F HAVQJWSGEOOVKZ-LLVKDONJSA-N 0.000 claims 1
- HAVQJWSGEOOVKZ-NSHDSACASA-N 5-chloro-6-[4-[4-(dimethylamino)butoxy]-2,6-difluorophenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@@H](C)C(F)(F)F)=C1C1=C(F)C=C(OCCCCN(C)C)C=C1F HAVQJWSGEOOVKZ-NSHDSACASA-N 0.000 claims 1
- LZZPXHJWPSSTMF-MRVPVSSYSA-N 6-[4-(3-aminopropoxy)-2,6-difluorophenyl]-5-chloro-n-[(2r)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@H](C)C(F)(F)F)=C1C1=C(F)C=C(OCCCN)C=C1F LZZPXHJWPSSTMF-MRVPVSSYSA-N 0.000 claims 1
- USLPKKDUHYSBFJ-LLVKDONJSA-N 6-[4-[3-(azetidin-1-yl)propoxy]-2,6-difluorophenyl]-5-chloro-n-[(2r)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@H](C)C(F)(F)F)=C1C(C(=C1)F)=C(F)C=C1OCCCN1CCC1 USLPKKDUHYSBFJ-LLVKDONJSA-N 0.000 claims 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims 1
- 102000029749 Microtubule Human genes 0.000 claims 1
- 108091022875 Microtubule Proteins 0.000 claims 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims 1
- 150000008046 alkali metal hydrides Chemical class 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000005907 cancer growth Effects 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 229940044683 chemotherapy drug Drugs 0.000 claims 1
- 230000006378 damage Effects 0.000 claims 1
- 150000004683 dihydrates Chemical class 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000001530 fumaric acid Substances 0.000 claims 1
- 230000026030 halogenation Effects 0.000 claims 1
- 238000005658 halogenation reaction Methods 0.000 claims 1
- 210000004688 microtubule Anatomy 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 230000001737 promoting effect Effects 0.000 claims 1
- 230000000087 stabilizing effect Effects 0.000 claims 1
- 239000001384 succinic acid Substances 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 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
- C07D487/02—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 two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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| US6255309B1 (en) * | 1999-03-19 | 2001-07-03 | American Cyanomid Co. | Fungicidal trifluoromethylalkylamino-triazolopyrimidines |
| JP2004502691A (ja) * | 2000-06-30 | 2004-01-29 | ワイス | 抗癌薬としての置換トリアゾロピリミジン |
| US7419982B2 (en) * | 2003-09-24 | 2008-09-02 | Wyeth Holdings Corporation | Crystalline forms of 5-chloro-6-{2,6-difluoro-4-[3-(methylamino)propoxy]phenyl}-N-[(1S)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine salts |
| BRPI0414700A (pt) | 2003-09-24 | 2006-11-14 | Wyeth Corp | 6-[(substituìdo)fenil]triazolopirimidinas como agentes anti-cáncer |
| MY179926A (en) * | 2003-12-08 | 2020-11-19 | Wyeth Corp | Process for the preparation of tubulin inhibitors |
| EP1891052A1 (en) * | 2005-06-13 | 2008-02-27 | Wyeth | Tubulin inhibitor and process for its preparation |
| CN101193884A (zh) | 2005-06-13 | 2008-06-04 | 惠氏公司 | 微管蛋白抑制剂和其制备方法 |
| CN101208289A (zh) * | 2005-06-27 | 2008-06-25 | 巴斯福股份公司 | 生产取代的苯基丙二酸酯中间体化合物的方法及其在生产5,7-二羟基-6-(2,4,6-三氟苯基)[1,2,4]三唑并[1,5-a]嘧啶中的用途 |
| WO2007075465A1 (en) * | 2005-12-16 | 2007-07-05 | Wyeth | Dimers and adducts of 6-[(substituted) phenyl] triazolopyrimidines useful as anticancer agents |
| TW200730530A (en) * | 2005-12-16 | 2007-08-16 | Wyeth Corp | Lyophilized compositions of a triazolopyrimidine compound |
| CN101600350A (zh) * | 2007-01-08 | 2009-12-09 | 巴斯夫欧洲公司 | 唑并嘧啶在防治植物病原性有害真菌中的用途 |
| WO2014047257A2 (en) | 2012-09-19 | 2014-03-27 | The Trustees Of The University Of Pennsylvania | Heterocyclic compounds and their use for the treatment of neurodegenerative tauopathies |
| WO2019169111A1 (en) | 2018-03-02 | 2019-09-06 | The Trustees Of The University Of Pennsylvania | [1,2,4]triazolo[1,5-a]pyrimidine compounds and use in stabilizing microtubules |
| AU2021255495A1 (en) * | 2020-04-14 | 2022-12-15 | The Regents Of The University Of California | Substituted {1,2,4,} triazolo{1,5-a} pyrimidine compounds and use in stabilizing microtubules |
| CN114369098B (zh) * | 2022-01-06 | 2023-03-10 | 苏州大学 | 一种三唑并嘧啶醇类化合物及其制备方法和应用 |
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| US5593996A (en) * | 1991-12-30 | 1997-01-14 | American Cyanamid Company | Triazolopyrimidine derivatives |
| TW224044B (enExample) | 1991-12-30 | 1994-05-21 | Shell Internat Res Schappej B V | |
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| IL108747A (en) | 1993-03-04 | 1999-03-12 | Shell Int Research | Mushroom-killing preparations containing a history of 6 metamorphoses of 5 - 7 Dihalo - 1, 2 - 4 Triazlo [A-1,5] Pyrimidine Certain such new compounds and their preparation |
| IL108731A (en) * | 1993-03-04 | 1997-03-18 | Shell Int Research | 6, N-DISUBSTITUTED-£1, 2, 4| TRIAZOLO-£1, 5-a| PYRIMIDINE- 7-AMINE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS FUNGICIDES |
| RU2147584C1 (ru) * | 1995-10-27 | 2000-04-20 | Американ Цианамид Компани | Способ получения дигалоидазолопиримидинов и способ получения дигидроксиазолопиримидинов |
| US5817663A (en) * | 1996-10-07 | 1998-10-06 | American Cyanamid Company | Pentafluorophenylazolopyrimidines |
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| AU6558498A (en) | 1997-03-18 | 1998-10-12 | American Cyanamid Company | Process for the preparation of arylmalonates |
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| TWI252231B (en) | 1997-04-14 | 2006-04-01 | American Cyanamid Co | Fungicidal trifluorophenyl-triazolopyrimidines |
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| TW460476B (en) | 1997-04-14 | 2001-10-21 | American Cyanamid Co | Fungicidal trifluoromethylalkylamino-triazolopyrimidines |
| US5948783A (en) * | 1997-04-14 | 1999-09-07 | American Cyanamid Company | Fungicidal trifluoromethylalkylamino-triazolopyrimidines |
| US5994360A (en) * | 1997-07-14 | 1999-11-30 | American Cyanamid Company | Fungicidal 5-alkyl-triazolopyrimidines |
| AU750489B2 (en) | 1998-02-11 | 2002-07-18 | Wyeth Holdings Corporation | Fungicidal 7-alkyl-triazolopyrimidines |
| US6020338A (en) * | 1998-02-11 | 2000-02-01 | American Cyanamid Company | Fungicidal 7-alkyl-triazolopyrimidines |
| US6124301A (en) * | 1998-03-17 | 2000-09-26 | American Cyanamid Company | Enhancement of the efficacy of triazolopyrimidines |
| JPH11322517A (ja) | 1998-03-17 | 1999-11-24 | American Cyanamid Co | トリアゾロピリミジン類の効力の増進 |
| US6284762B1 (en) * | 1998-03-23 | 2001-09-04 | American Cyanamid Company | Fungicidal 6-(2-halo-4-alkoxyphenyl)-triazolopyrimidines |
| WO1999048893A1 (en) | 1998-03-23 | 1999-09-30 | American Cyanamid Company | Fungicidal 6-(2-halo-4-alkoxyphenyl)-triazolopyrimidines |
| US5981534A (en) * | 1998-09-25 | 1999-11-09 | American Cyanamid Company | Fungicidal 6-(2,6-difluoro-4-alkoxyphenyl)-triazolopyrimidines |
| US6117865A (en) * | 1998-09-10 | 2000-09-12 | American Cyanamid Company | Fungicidal trifluorophenyl-triazolopyrimidines |
| US6268371B1 (en) * | 1998-09-10 | 2001-07-31 | American Cyanamid Co. | Fungicidal mixtures |
| US5985883A (en) * | 1998-09-25 | 1999-11-16 | American Cyanamid Company | Fungicidal trichlorophenyl-triazolopyrimidines |
| JP2000103790A (ja) | 1998-09-25 | 2000-04-11 | American Cyanamid Co | 殺菌・殺カビ性のトリハロフェニル―トリアゾロピリミジン類 |
| US5986135A (en) * | 1998-09-25 | 1999-11-16 | American Cyanamid Company | Fungicidal trifluoromethylalkylamino-triazolopyrimidines |
| US6242451B1 (en) * | 1998-09-25 | 2001-06-05 | Klaus-Juergen Pees | Fungicidal trihalophenyl-triazolopyrimidines |
| DE69914364T2 (de) | 1998-09-25 | 2004-07-22 | Basf Ag | Nicht-wässriges suspensionskonzentrat |
| SI0988790T1 (en) | 1998-09-25 | 2003-10-31 | Basf Aktiengesellschaft | Fungicidal mixtures |
| US6277856B1 (en) * | 1998-09-25 | 2001-08-21 | American Cynamid Co. | Fungicidal mixtures |
| US6521628B1 (en) * | 1999-01-29 | 2003-02-18 | Basf Aktiengesellschaft | Fungicidal mixtures |
| US6699874B2 (en) * | 1999-09-24 | 2004-03-02 | Basf Aktiengesellschaft | Fungicidal mixtures |
| WO2001035738A2 (en) * | 1999-11-18 | 2001-05-25 | Basf Corporation | Non-aqueous concentrated spreading oil composition |
| US6559151B2 (en) * | 2000-05-08 | 2003-05-06 | Basf Aktiengesellschaft | 6-(2-trifluoromethyl-phenyl)-triazolopyrimidines |
| JP2004502691A (ja) * | 2000-06-30 | 2004-01-29 | ワイス | 抗癌薬としての置換トリアゾロピリミジン |
| MXPA03001263A (es) * | 2000-08-25 | 2003-06-24 | Basf Ag | Formulacion fungicida. |
| US6459602B1 (en) * | 2000-10-26 | 2002-10-01 | O2 Micro International Limited | DC-to-DC converter with improved transient response |
| EP1368351A2 (de) | 2000-11-13 | 2003-12-10 | Basf Aktiengesellschaft | 7-(r)-amino-triazolopyrimidine, deren herstellung und verwendung zur bekämpfung von pflanzenpathogenen pilzen |
| TR200402494T4 (tr) | 2000-12-06 | 2004-12-21 | Wyeth | Mantar öldürücü 6-(2-triflorometil-fenil)-triazolopirimidinler. |
| DE10063115A1 (de) * | 2000-12-18 | 2002-06-27 | Bayer Ag | Triazolopyrimidine |
| WO2002067679A1 (en) | 2001-02-19 | 2002-09-06 | Basf Aktiengesellschaft | Fungicidal mixtures |
| ES2236509T3 (es) | 2001-04-11 | 2005-07-16 | Basf Aktiengesellschaft | 5-halogen-6-fenil-7-fluoroalquilamino-triazolopirimidinas utiles como fungicidas. |
| DE10124208A1 (de) * | 2001-05-18 | 2002-11-21 | Bayer Ag | Verwendung von Triazolopyrimidin-Derivaten als Mikrobizide |
| US7038047B2 (en) | 2001-07-18 | 2006-05-02 | Basf Aktiengesellschaft | Substituted 6-(2-methoxyphenyl) triazolopyrimides as fungicides |
| BRPI0414700A (pt) | 2003-09-24 | 2006-11-14 | Wyeth Corp | 6-[(substituìdo)fenil]triazolopirimidinas como agentes anti-cáncer |
-
2004
- 2004-09-17 BR BRPI0414700-6A patent/BRPI0414700A/pt not_active IP Right Cessation
- 2004-09-17 PL PL04788820T patent/PL1680425T3/pl unknown
- 2004-09-17 ES ES04788820T patent/ES2279452T3/es not_active Expired - Lifetime
- 2004-09-17 CA CA002539252A patent/CA2539252A1/en not_active Abandoned
- 2004-09-17 RU RU2006107579/04A patent/RU2006107579A/ru not_active Application Discontinuation
- 2004-09-17 EP EP04788820A patent/EP1680425B1/en not_active Expired - Lifetime
- 2004-09-17 PT PT04788820T patent/PT1680425E/pt unknown
- 2004-09-17 SI SI200430195T patent/SI1680425T1/sl unknown
- 2004-09-17 CN CNB2004800302006A patent/CN100519559C/zh not_active Expired - Fee Related
- 2004-09-17 AU AU2004276240A patent/AU2004276240A1/en not_active Withdrawn
- 2004-09-17 KR KR1020067005785A patent/KR20060098368A/ko not_active Withdrawn
- 2004-09-17 MX MXPA06003206A patent/MXPA06003206A/es active IP Right Grant
- 2004-09-17 DK DK04788820T patent/DK1680425T3/da active
- 2004-09-17 DE DE602004004295T patent/DE602004004295T8/de active Active
- 2004-09-17 JP JP2006528075A patent/JP2007506744A/ja not_active Withdrawn
- 2004-09-17 WO PCT/US2004/030515 patent/WO2005030775A1/en not_active Ceased
- 2004-09-21 TW TW093128500A patent/TW200512211A/zh unknown
- 2004-09-22 SA SA04250302A patent/SA04250302A/ar unknown
- 2004-09-23 AR ARP040103440A patent/AR045810A1/es not_active Application Discontinuation
- 2004-09-23 PE PE2004000925A patent/PE20050433A1/es not_active Application Discontinuation
- 2004-09-24 PA PA20048613301A patent/PA8613301A1/es unknown
- 2004-09-24 GT GT200400190A patent/GT200400190A/es unknown
- 2004-09-24 US US10/950,543 patent/US7507739B2/en not_active Expired - Fee Related
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2006
- 2006-03-13 IL IL174281A patent/IL174281A0/en unknown
- 2006-03-14 CR CR8288A patent/CR8288A/es not_active Application Discontinuation
- 2006-03-23 NO NO20061318A patent/NO20061318L/no not_active Application Discontinuation
- 2006-03-23 ZA ZA200602387A patent/ZA200602387B/xx unknown
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- 2006-04-21 CO CO06038133A patent/CO5690598A2/es not_active Application Discontinuation
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| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
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