ZA200305619B - Substituted triazole diamine derivatives as kinase inhibitors. - Google Patents
Substituted triazole diamine derivatives as kinase inhibitors. Download PDFInfo
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- ZA200305619B ZA200305619B ZA200305619A ZA200305619A ZA200305619B ZA 200305619 B ZA200305619 B ZA 200305619B ZA 200305619 A ZA200305619 A ZA 200305619A ZA 200305619 A ZA200305619 A ZA 200305619A ZA 200305619 B ZA200305619 B ZA 200305619B
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- South Africa
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- alkyl
- amino
- substituted
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- -1 triazole diamine Chemical class 0.000 title claims description 44
- 229940043355 kinase inhibitor Drugs 0.000 title description 6
- 239000003757 phosphotransferase inhibitor Substances 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 566
- 125000001424 substituent group Chemical group 0.000 claims description 488
- 229910052739 hydrogen Inorganic materials 0.000 claims description 345
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 305
- 239000001257 hydrogen Substances 0.000 claims description 271
- 125000001072 heteroaryl group Chemical group 0.000 claims description 223
- 229910052799 carbon Inorganic materials 0.000 claims description 222
- 125000003118 aryl group Chemical group 0.000 claims description 220
- 125000000623 heterocyclic group Chemical group 0.000 claims description 199
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 166
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 153
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 149
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 146
- 150000002431 hydrogen Chemical group 0.000 claims description 109
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 100
- 125000003545 alkoxy group Chemical group 0.000 claims description 87
- 150000001875 compounds Chemical class 0.000 claims description 77
- 125000003342 alkenyl group Chemical group 0.000 claims description 72
- 125000000304 alkynyl group Chemical group 0.000 claims description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 108091000080 Phosphotransferase Proteins 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 26
- 102000020233 phosphotransferase Human genes 0.000 claims description 26
- 238000011282 treatment Methods 0.000 claims description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 230000001404 mediated effect Effects 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 13
- 125000001544 thienyl group Chemical group 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 125000000335 thiazolyl group Chemical group 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 102000003903 Cyclin-dependent kinases Human genes 0.000 claims description 6
- 108090000266 Cyclin-dependent kinases Proteins 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 4
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 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 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 123
- 125000001475 halogen functional group Chemical group 0.000 claims 118
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 43
- 239000000203 mixture Substances 0.000 claims 21
- 239000000126 substance Substances 0.000 claims 18
- 206010028980 Neoplasm Diseases 0.000 claims 9
- 239000002246 antineoplastic agent Substances 0.000 claims 9
- 229940127089 cytotoxic agent Drugs 0.000 claims 9
- 108010034798 CDC2 Protein Kinase Proteins 0.000 claims 6
- 108010024986 Cyclin-Dependent Kinase 2 Proteins 0.000 claims 6
- 108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 claims 6
- 102100032857 Cyclin-dependent kinase 1 Human genes 0.000 claims 6
- 102100036239 Cyclin-dependent kinase 2 Human genes 0.000 claims 6
- 102100036252 Cyclin-dependent kinase 4 Human genes 0.000 claims 6
- 101001012157 Homo sapiens Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 claims 6
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims 6
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims 6
- 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 claims 6
- 102000016549 Vascular Endothelial Growth Factor Receptor-2 Human genes 0.000 claims 6
- 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims 6
- 201000011510 cancer Diseases 0.000 claims 6
- 230000005764 inhibitory process Effects 0.000 claims 6
- 102000009484 Vascular Endothelial Growth Factor Receptors Human genes 0.000 claims 5
- 108010034265 Vascular Endothelial Growth Factor Receptors Proteins 0.000 claims 5
- 206010059245 Angiopathy Diseases 0.000 claims 3
- 230000033115 angiogenesis Effects 0.000 claims 3
- 230000005907 cancer growth Effects 0.000 claims 3
- 238000002512 chemotherapy Methods 0.000 claims 3
- 208000022605 chemotherapy-induced alopecia Diseases 0.000 claims 3
- 230000009977 dual effect Effects 0.000 claims 3
- 238000001959 radiotherapy Methods 0.000 claims 3
- 208000037803 restenosis Diseases 0.000 claims 3
- 230000004614 tumor growth Effects 0.000 claims 3
- 125000004512 1,2,3-thiadiazol-4-yl group Chemical group S1N=NC(=C1)* 0.000 claims 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- ZUNASHLZAWVKEM-UHFFFAOYSA-N 4-[[5-amino-1-(2-chloro-6-fluoro-3-methylbenzoyl)-1,2,4-triazol-3-yl]amino]benzenesulfonamide Chemical compound CC1=CC=C(F)C(C(=O)N2C(=NC(NC=3C=CC(=CC=3)S(N)(=O)=O)=N2)N)=C1Cl ZUNASHLZAWVKEM-UHFFFAOYSA-N 0.000 claims 1
- ARIOBGGRZJITQX-UHFFFAOYSA-N 5-amino-3-{[4-(aminosulfonyl)phenyl]amino}-n-(2,6-difluorophenyl)-1h-1,2,4-triazole-1-carbothioamide Chemical compound N=1N(C(=S)NC=2C(=CC=CC=2F)F)C(N)=NC=1NC1=CC=C(S(N)(=O)=O)C=C1 ARIOBGGRZJITQX-UHFFFAOYSA-N 0.000 claims 1
- JBOXDNIWQACYPW-UHFFFAOYSA-N 5-amino-n-(2,6-difluorophenyl)-3-(4-sulfamoylanilino)-1,2,4-triazole-1-carboxamide Chemical compound N=1N(C(=O)NC=2C(=CC=CC=2F)F)C(N)=NC=1NC1=CC=C(S(N)(=O)=O)C=C1 JBOXDNIWQACYPW-UHFFFAOYSA-N 0.000 claims 1
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims 1
- 102000016736 Cyclin Human genes 0.000 claims 1
- 108050006400 Cyclin Proteins 0.000 claims 1
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 230000003511 endothelial effect Effects 0.000 claims 1
- 230000012010 growth Effects 0.000 claims 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 102000005962 receptors Human genes 0.000 claims 1
- 108020003175 receptors Proteins 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 126
- 125000005843 halogen group Chemical group 0.000 description 123
- 125000002723 alicyclic group Chemical group 0.000 description 8
- 125000002950 monocyclic group Chemical group 0.000 description 7
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 125000003367 polycyclic group Chemical group 0.000 description 5
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 125000002837 carbocyclic group Chemical group 0.000 description 4
- 229940127263 dual kinase inhibitor Drugs 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 229920000180 alkyd Polymers 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000003831 tetrazolyl group Chemical group 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 108091007911 GSKs Proteins 0.000 description 2
- 102000004103 Glycogen Synthase Kinases Human genes 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- PKWIYNIDEDLDCJ-UHFFFAOYSA-N guanazole Chemical class NC1=NNC(N)=N1 PKWIYNIDEDLDCJ-UHFFFAOYSA-N 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 125000002757 morpholinyl group Chemical group 0.000 description 2
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 125000004344 phenylpropyl group Chemical group 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 229910052717 sulfur Chemical group 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- QHHHLHCCVDMOJI-UHFFFAOYSA-N 1,3-thiazol-4-amine Chemical class NC1=CSC=N1 QHHHLHCCVDMOJI-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000000579 2,2-diphenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
- 108091007914 CDKs Proteins 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- NRWBBYXZLGNRBM-UHFFFAOYSA-N amino 3-amino-1h-1,2,4-triazole-5-carboxylate Chemical compound NOC(=O)C1=NNC(N)=N1 NRWBBYXZLGNRBM-UHFFFAOYSA-N 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 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
- 201000010099 disease Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000004475 heteroaralkyl group Chemical group 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 125000006301 indolyl methyl group Chemical group 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000000394 phosphonato group Chemical group [O-]P([O-])(*)=O 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 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
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/14—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25770300P | 2000-12-22 | 2000-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200305619B true ZA200305619B (en) | 2004-10-21 |
Family
ID=22977396
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200305619A ZA200305619B (en) | 2000-12-22 | 2003-07-21 | Substituted triazole diamine derivatives as kinase inhibitors. |
Country Status (23)
| Country | Link |
|---|---|
| US (2) | US6924302B2 (cs) |
| EP (1) | EP1355889B1 (cs) |
| CN (1) | CN100357278C (cs) |
| AT (1) | ATE328874T1 (cs) |
| BG (2) | BG107959A (cs) |
| BR (1) | BR0116792A (cs) |
| CA (1) | CA2432870A1 (cs) |
| CZ (1) | CZ20031941A3 (cs) |
| DE (1) | DE60120494T2 (cs) |
| DK (1) | DK1355889T3 (cs) |
| ES (1) | ES2266313T3 (cs) |
| HU (1) | HUP0303868A3 (cs) |
| IL (1) | IL156584A0 (cs) |
| MX (1) | MXPA03005777A (cs) |
| NO (1) | NO20032848L (cs) |
| NZ (1) | NZ526624A (cs) |
| PL (1) | PL363316A1 (cs) |
| PT (1) | PT1355889E (cs) |
| RU (1) | RU2274639C2 (cs) |
| SK (1) | SK9062003A3 (cs) |
| WO (1) | WO2002057240A1 (cs) |
| YU (1) | YU51803A (cs) |
| ZA (1) | ZA200305619B (cs) |
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| MXPA05012275A (es) | 2003-05-13 | 2006-02-10 | Depuy Spine Inc | Un metodo para tratar enfermedad degenerativa del disco. |
| US7553827B2 (en) | 2003-08-13 | 2009-06-30 | Depuy Spine, Inc. | Transdiscal administration of cycline compounds |
| US8273347B2 (en) | 2003-05-13 | 2012-09-25 | Depuy Spine, Inc. | Autologous treatment of degenerated disc with cells |
| US8361467B2 (en) | 2003-07-30 | 2013-01-29 | Depuy Spine, Inc. | Trans-capsular administration of high specificity cytokine inhibitors into orthopedic joints |
| DE602004025258D1 (de) | 2003-08-06 | 2010-03-11 | Vertex Pharma | Aminotriazol-verbindungen als proteinkinase-hemmer |
| US8895540B2 (en) | 2003-11-26 | 2014-11-25 | DePuy Synthes Products, LLC | Local intraosseous administration of bone forming agents and anti-resorptive agents, and devices therefor |
| DE10356579A1 (de) * | 2003-12-04 | 2005-07-07 | Merck Patent Gmbh | Aminderivate |
| WO2005070042A2 (en) * | 2004-01-09 | 2005-08-04 | Smithkline Beecham Corporation | Novel chemical compounds |
| EP2260849A1 (en) | 2004-01-21 | 2010-12-15 | Emory University | Compositions and methods of use for tyrosine kinase inhibitors to treat pathogenic infection |
| EP1720843A2 (en) * | 2004-02-11 | 2006-11-15 | Janssen Pharmaceutica N.V. | Process for the preparation of substituted triazole compounds |
| MX2007004155A (es) * | 2004-10-08 | 2007-09-11 | Johnson & Johnson | Derivados de 1,2,4-triazoloaminoaril (heteroaril) sulfonamida. |
| SI1811998T1 (sl) * | 2004-10-21 | 2011-01-31 | Vertex Pharma | Triazoli uporabni kot inhibitorji proteinskih kinaz |
| DE102004055998A1 (de) | 2004-11-19 | 2006-05-24 | Rheinische Friedrich-Wilhelms-Universität Bonn | Niedermolekulare Inhibitoren von Guaninnucleotid-Austauschfaktoren der Cytohesin-Familie |
| KR101346886B1 (ko) | 2005-01-21 | 2014-01-02 | 아스텍스 테라퓨틱스 리미티드 | 제약 화합물 |
| EP1922310A2 (en) * | 2005-09-07 | 2008-05-21 | Rigel Pharmaceuticals, Inc. | Triazole derivatives useful as axl inhibitors |
| EP2045253A4 (en) | 2006-06-29 | 2013-01-23 | Nissan Chemical Ind Ltd | alpha-amino acid derivative and pharmaceutical agent containing it as an active ingredient |
| US8916552B2 (en) | 2006-10-12 | 2014-12-23 | Astex Therapeutics Limited | Pharmaceutical combinations |
| WO2008044045A1 (en) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical combinations |
| DE102006054205A1 (de) * | 2006-11-15 | 2008-05-29 | Rheinische Friedrich-Wilhelms Universität | Verwendung von Cytohesin-Inhibitoren zur chemischen Induktion von Langlebigkeit |
| CA2695613A1 (en) | 2006-12-19 | 2008-06-26 | Pharmos Corporation | Sulfonamide derivatives with therapeutic indications |
| PT2114955E (pt) | 2006-12-29 | 2013-04-18 | Rigel Pharmaceuticals Inc | Triazoles substituídos com arilo bicíclico em ponte ou heteroarilo bicíclico em ponte úteis como inibidores de axl |
| WO2008083353A1 (en) | 2006-12-29 | 2008-07-10 | Rigel Pharmaceuticals, Inc. | Bicyclic aryl and bicyclic heteroaryl substituted triazoles useful as axl inhibitors |
| PL2078010T3 (pl) | 2006-12-29 | 2014-07-31 | Rigel Pharmaceuticals Inc | Triazole podstawione policyklicznym heteroarylem użyteczne jako inhibitory Axl |
| CN101622252B (zh) | 2006-12-29 | 2015-04-22 | 里格尔制药公司 | 用作axl抑制剂的取代三唑 |
| EP2484679B1 (en) * | 2006-12-29 | 2016-09-28 | Rigel Pharmaceuticals, Inc. | N3-heteroaryl substituted triazoles and n5-heteroaryl substitued triazoles useful as axl inhibitors |
| ES2424023T3 (es) | 2007-10-18 | 2013-09-26 | Janssen Pharmaceutica N.V. | 1,2,4-triazoles trisustituidos |
| JO2784B1 (en) | 2007-10-18 | 2014-03-15 | شركة جانسين فارماسوتيكا ان. في | 5,3,1 - Triazole substitute derivative |
| US7935693B2 (en) | 2007-10-26 | 2011-05-03 | Rigel Pharmaceuticals, Inc. | Polycyclic aryl substituted triazoles and polycyclic heteroaryl substituted triazoles useful as Axl inhibitors |
| US8986696B2 (en) | 2007-12-21 | 2015-03-24 | Depuy Mitek, Inc. | Trans-capsular administration of p38 map kinase inhibitors into orthopedic joints |
| KR101247840B1 (ko) | 2008-02-22 | 2013-03-26 | 에프. 호프만-라 로슈 아게 | 아밀로이드 베타 조절제 |
| TWI433847B (zh) | 2008-03-19 | 2014-04-11 | Janssen Pharmaceutica Nv | 經三取代之１，２，４－三唑類 |
| US8779158B2 (en) | 2008-05-09 | 2014-07-15 | Janssen Pharmaceutica Nv | Trisubstituted pyrazoles as acetylcholine receptor modulators |
| US8349838B2 (en) * | 2008-07-09 | 2013-01-08 | Rigel Pharmaceuticals, Inc. | Polycyclic heteroaryl substituted triazoles useful as Axl inhibitors |
| SI2328888T1 (sl) | 2008-07-09 | 2013-03-29 | Rigel Pharmaceuticals, Inc. | Premoščeni biciklični heteroaril substituirani triazoli, uporabni kot inhibitorji Axl |
| EP2334665B1 (en) | 2008-10-09 | 2013-07-10 | F. Hoffmann-La Roche AG | Modulators for amyloid beta |
| KR101293421B1 (ko) * | 2008-11-10 | 2013-08-05 | 에프. 호프만-라 로슈 아게 | 헤테로사이클릭 감마 분비효소 조절제 |
| AU2010204578B2 (en) | 2009-01-16 | 2016-05-12 | Rigel Pharmaceuticals, Inc. | AXL inhibitors for use in combination therapy for preventing, treating or managing metastatic cancer |
| US8486967B2 (en) | 2010-02-17 | 2013-07-16 | Hoffmann-La Roche Inc. | Heteroaryl substituted piperidines |
| US20140010783A1 (en) * | 2012-07-06 | 2014-01-09 | Hoffmann-La Roche Inc. | Antiviral compounds |
| AU2013337370B2 (en) * | 2012-11-05 | 2018-03-29 | Nantbioscience, Inc. | Cyclic sulfonamide containing derivatives as inhibitors of hedgehog signaling pathway |
| BR112015021432A2 (pt) * | 2013-03-05 | 2017-07-18 | Hoffmann La Roche | compostos antivirais |
| RU2015137966A (ru) * | 2013-03-06 | 2017-04-06 | Ф. Хоффманн-Ля Рош Аг | Противовирусные соединения |
| WO2018175670A1 (en) | 2017-03-22 | 2018-09-27 | The Research Foundation For The State University Of New York | Matrix metalloproteinase-9 hemopexin domain inhibitors and methods of treatment using same |
| US12110278B2 (en) * | 2020-10-13 | 2024-10-08 | Yale University | Selective JAK2 pseudokinase ligands and methods of use |
| WO2023076219A2 (en) * | 2021-10-26 | 2023-05-04 | Vasocardea, Inc. | Antagonists of gpr39 protein |
| CN114292243B (zh) * | 2022-01-12 | 2023-11-21 | 中山大学 | 一种三唑类衍生物或其药学上可接受的盐及其制备方法和应用 |
| CN115433222A (zh) * | 2022-09-20 | 2022-12-06 | 五邑大学 | 一种2-(偕二氟丙烯)苯甲酰胺类化合物的制备方法及其应用 |
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| US2352944A (en) * | 1942-07-04 | 1944-07-04 | Gen Electric | Triazole derivatives |
| NL301383A (cs) | 1962-12-06 | |||
| US4727022A (en) * | 1984-03-14 | 1988-02-23 | Syntex (U.S.A.) Inc. | Methods for modulating ligand-receptor interactions and their application |
| US5196351A (en) * | 1987-09-30 | 1993-03-23 | Beckman Instruments, Inc. | Bidentate conjugate and method of use thereof |
| HU206095B (en) * | 1989-10-25 | 1992-08-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing triazolylcarboxylc acid hydrazie and semicarbazide derivatives and pharmaceutical compositions comprising same |
| HU206096B (en) * | 1989-11-24 | 1992-08-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing triazolylcarboxylic acid thioamide derivatives and pharmaceutical compositions comprising same |
| US5683867A (en) * | 1990-06-11 | 1997-11-04 | Nexstar Pharmaceuticals, Inc. | Systematic evolution of ligands by exponential enrichment: blended SELEX |
| DE69233750D1 (de) * | 1991-04-10 | 2009-01-02 | Scripps Research Inst | Bibliotheken heterodimerer Rezeptoren mittels Phagemiden |
| ES2139605T3 (es) * | 1991-09-02 | 2000-02-16 | Yamanouchi Pharma Co Ltd | Amina terciaria triazolilada o una sal de esta. |
| US5543507A (en) * | 1992-03-05 | 1996-08-06 | Isis Pharmaceuticals, Inc. | Covalently cross-linked oligonucleotides |
| US5362859A (en) * | 1992-07-27 | 1994-11-08 | Sepracor, Inc. | High-capacity affinity supports and methods for the preparation and use of same |
| US5512435A (en) * | 1993-02-05 | 1996-04-30 | Renschler; Markus F. | Receptor-binding antiproliferative peptides |
| WO1995003286A1 (en) | 1993-07-23 | 1995-02-02 | The Green Cross Corporation | Triazole derivative and pharmaceutical use thereof |
| US5698401A (en) * | 1995-11-14 | 1997-12-16 | Abbott Laboratories | Use of nuclear magnetic resonance to identify ligands to target biomolecules |
| KR20010082501A (ko) | 1997-10-27 | 2001-08-30 | 개리 이. 프라이드만 | 4-아미노티아졸 유도체, 그 제조방법 및 싸이클린-의존성키나아제의 억제제로서의 이용방법 |
| GB9918180D0 (en) | 1999-08-02 | 1999-10-06 | Smithkline Beecham Plc | Novel compositions |
-
2001
- 2001-12-21 SK SK906-2003A patent/SK9062003A3/sk not_active Application Discontinuation
- 2001-12-21 PL PL01363316A patent/PL363316A1/xx not_active Application Discontinuation
- 2001-12-21 US US10/029,750 patent/US6924302B2/en not_active Expired - Lifetime
- 2001-12-21 NZ NZ526624A patent/NZ526624A/en not_active IP Right Cessation
- 2001-12-21 DK DK01998116T patent/DK1355889T3/da active
- 2001-12-21 EP EP01998116A patent/EP1355889B1/en not_active Expired - Lifetime
- 2001-12-21 PT PT01998116T patent/PT1355889E/pt unknown
- 2001-12-21 RU RU2003118448/04A patent/RU2274639C2/ru not_active IP Right Cessation
- 2001-12-21 IL IL15658401A patent/IL156584A0/xx unknown
- 2001-12-21 CA CA002432870A patent/CA2432870A1/en not_active Abandoned
- 2001-12-21 AT AT01998116T patent/ATE328874T1/de active
- 2001-12-21 CN CNB018226450A patent/CN100357278C/zh not_active Expired - Fee Related
- 2001-12-21 BR BR0116792-8A patent/BR0116792A/pt not_active IP Right Cessation
- 2001-12-21 CZ CZ20031941A patent/CZ20031941A3/cs unknown
- 2001-12-21 YU YU51803A patent/YU51803A/sh unknown
- 2001-12-21 WO PCT/US2001/050559 patent/WO2002057240A1/en active IP Right Grant
- 2001-12-21 ES ES01998116T patent/ES2266313T3/es not_active Expired - Lifetime
- 2001-12-21 HU HU0303868A patent/HUP0303868A3/hu unknown
- 2001-12-21 MX MXPA03005777A patent/MXPA03005777A/es active IP Right Grant
- 2001-12-21 DE DE60120494T patent/DE60120494T2/de not_active Expired - Lifetime
-
2003
- 2003-06-20 NO NO20032848A patent/NO20032848L/no not_active Application Discontinuation
- 2003-07-01 BG BG107959A patent/BG107959A/bg unknown
- 2003-07-08 BG BG107985A patent/BG107985A/bg unknown
- 2003-07-21 ZA ZA200305619A patent/ZA200305619B/en unknown
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2005
- 2005-02-01 US US11/047,800 patent/US7317031B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| RU2274639C2 (ru) | 2006-04-20 |
| SK9062003A3 (en) | 2004-04-06 |
| BR0116792A (pt) | 2004-02-17 |
| ATE328874T1 (de) | 2006-06-15 |
| NZ526624A (en) | 2005-07-29 |
| ES2266313T3 (es) | 2007-03-01 |
| NO20032848L (no) | 2003-08-20 |
| HK1057373A1 (en) | 2004-04-02 |
| PT1355889E (pt) | 2006-09-29 |
| US7317031B2 (en) | 2008-01-08 |
| US20050182116A1 (en) | 2005-08-18 |
| NO20032848D0 (no) | 2003-06-20 |
| BG107985A (bg) | 2004-11-30 |
| CA2432870A1 (en) | 2002-07-25 |
| EP1355889A1 (en) | 2003-10-29 |
| WO2002057240A1 (en) | 2002-07-25 |
| DE60120494T2 (de) | 2006-12-21 |
| EP1355889B1 (en) | 2006-06-07 |
| CZ20031941A3 (cs) | 2004-08-18 |
| CN100357278C (zh) | 2007-12-26 |
| PL363316A1 (en) | 2004-11-15 |
| DE60120494D1 (de) | 2006-07-20 |
| BG107959A (bg) | 2004-12-30 |
| YU51803A (sh) | 2006-05-25 |
| MXPA03005777A (es) | 2005-02-14 |
| RU2003118448A (ru) | 2005-01-27 |
| HUP0303868A2 (hu) | 2004-03-01 |
| DK1355889T3 (da) | 2006-10-09 |
| US6924302B2 (en) | 2005-08-02 |
| CN1575284A (zh) | 2005-02-02 |
| IL156584A0 (en) | 2004-01-04 |
| US20040077699A1 (en) | 2004-04-22 |
| HUP0303868A3 (en) | 2008-03-28 |
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