ZA200707730B - 1,2,4-triazine derivatives, preparation and use thereof in human therapy - Google Patents
1,2,4-triazine derivatives, preparation and use thereof in human therapy Download PDFInfo
- Publication number
- ZA200707730B ZA200707730B ZA200707730A ZA200707730A ZA200707730B ZA 200707730 B ZA200707730 B ZA 200707730B ZA 200707730 A ZA200707730 A ZA 200707730A ZA 200707730 A ZA200707730 A ZA 200707730A ZA 200707730 B ZA200707730 B ZA 200707730B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- ethyl
- dioxo
- triazin
- tetrahydro
- Prior art date
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- 150000003920 1,2,4-triazines Chemical class 0.000 title description 2
- 238000002560 therapeutic procedure Methods 0.000 title description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 100
- -1 alkenyl radical Chemical class 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 150000001721 carbon Chemical group 0.000 claims description 8
- 229910052717 sulfur Chemical group 0.000 claims description 8
- 239000011593 sulfur Chemical group 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 150000002825 nitriles Chemical class 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 102000023984 PPAR alpha Human genes 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 2
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 2
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 2
- 208000008589 Obesity Diseases 0.000 claims description 2
- 108010028924 PPAR alpha Proteins 0.000 claims description 2
- 102000000536 PPAR gamma Human genes 0.000 claims description 2
- 108010016731 PPAR gamma Proteins 0.000 claims description 2
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 230000032683 aging Effects 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims description 2
- 201000008980 hyperinsulinism Diseases 0.000 claims description 2
- 208000006575 hypertriglyceridemia Diseases 0.000 claims description 2
- 230000002757 inflammatory effect Effects 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 235000020824 obesity Nutrition 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 6
- 229910052794 bromium Inorganic materials 0.000 claims 5
- 229910052801 chlorine Inorganic materials 0.000 claims 5
- SSPYSWLZOPCOLO-UHFFFAOYSA-N 6-azauracil Chemical compound O=C1C=NNC(=O)N1 SSPYSWLZOPCOLO-UHFFFAOYSA-N 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 229940079593 drug Drugs 0.000 claims 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 229910052740 iodine Inorganic materials 0.000 claims 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- 238000006751 Mitsunobu reaction Methods 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- IMHBYKMAHXWHRP-UHFFFAOYSA-N anilazine Chemical compound ClC1=CC=CC=C1NC1=NC(Cl)=NC(Cl)=N1 IMHBYKMAHXWHRP-UHFFFAOYSA-N 0.000 claims 2
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 claims 2
- 229940017219 methyl propionate Drugs 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 150000003254 radicals Chemical class 0.000 claims 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 1
- IVFPHZYXZYQYNI-UHFFFAOYSA-N 2,4-dimethyl-1,2,4-triazine-3,5-dione Chemical compound CN1N=CC(=O)N(C)C1=O IVFPHZYXZYQYNI-UHFFFAOYSA-N 0.000 claims 1
- JODYTKSGBYJQGB-UHFFFAOYSA-N 2-[3-[4-[[2-heptyl-3,5-dioxo-4-(4,4,4-trifluorobutyl)-1,2,4-triazin-6-yl]amino]butyl]phenoxy]-2-methylpropanoic acid Chemical compound O=C1N(CCCC(F)(F)F)C(=O)N(CCCCCCC)N=C1NCCCCC1=CC=CC(OC(C)(C)C(O)=O)=C1 JODYTKSGBYJQGB-UHFFFAOYSA-N 0.000 claims 1
- OVZZGPNMQGHUBX-UHFFFAOYSA-N 2-[4-[2-[(2-heptyl-4-methyl-3,5-dioxo-1,2,4-triazin-6-yl)amino]ethyl]phenyl]sulfanyl-2-methylpropanoic acid Chemical compound O=C1N(C)C(=O)N(CCCCCCC)N=C1NCCC1=CC=C(SC(C)(C)C(O)=O)C=C1 OVZZGPNMQGHUBX-UHFFFAOYSA-N 0.000 claims 1
- XLSRHCBOXISETL-UHFFFAOYSA-N 2-[4-[2-[(4-butyl-2-heptyl-3,5-dioxo-1,2,4-triazin-6-yl)amino]ethyl]phenyl]sulfanyl-2-methylpropanoic acid Chemical compound O=C1N(CCCC)C(=O)N(CCCCCCC)N=C1NCCC1=CC=C(SC(C)(C)C(O)=O)C=C1 XLSRHCBOXISETL-UHFFFAOYSA-N 0.000 claims 1
- KHBDYJQGKLGFOQ-UHFFFAOYSA-N 2-methyl-2-[3-[4-[[2-methyl-3,5-dioxo-4-(4,4,4-trifluorobutyl)-1,2,4-triazin-6-yl]amino]butyl]phenyl]sulfanylpropanoic acid Chemical compound O=C1N(CCCC(F)(F)F)C(=O)N(C)N=C1NCCCCC1=CC=CC(SC(C)(C)C(O)=O)=C1 KHBDYJQGKLGFOQ-UHFFFAOYSA-N 0.000 claims 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 208000002874 Acne Vulgaris Diseases 0.000 claims 1
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- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
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- KQNPFQTWMSNSAP-UHFFFAOYSA-N alpha-isobutyric acid Natural products CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 230000017858 demethylation Effects 0.000 claims 1
- 238000010520 demethylation reaction Methods 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- NOJMHFASRURCAK-UHFFFAOYSA-N ethyl 2-[3-[2-[(2-heptyl-4-methyl-3,5-dioxo-1,2,4-triazin-6-yl)amino]ethyl]phenoxy]-2-methylpropanoate Chemical compound O=C1N(C)C(=O)N(CCCCCCC)N=C1NCCC1=CC=CC(OC(C)(C)C(=O)OCC)=C1 NOJMHFASRURCAK-UHFFFAOYSA-N 0.000 claims 1
- CAYLMGKSVYIJQV-UHFFFAOYSA-N ethyl 2-[3-[2-[(4-heptyl-2-methyl-3,5-dioxo-1,2,4-triazin-6-yl)amino]ethyl]phenoxy]-2-methylpropanoate Chemical compound CN1C(=O)N(CCCCCCC)C(=O)C(NCCC=2C=C(OC(C)(C)C(=O)OCC)C=CC=2)=N1 CAYLMGKSVYIJQV-UHFFFAOYSA-N 0.000 claims 1
- BKLRWPGKNLRKCE-UHFFFAOYSA-N ethyl 2-[3-[3-[(2-benzyl-4-heptyl-3,5-dioxo-1,2,4-triazin-6-yl)amino]propyl]phenoxy]-2-methylpropanoate Chemical compound N=1N(CC=2C=CC=CC=2)C(=O)N(CCCCCCC)C(=O)C=1NCCCC1=CC=CC(OC(C)(C)C(=O)OCC)=C1 BKLRWPGKNLRKCE-UHFFFAOYSA-N 0.000 claims 1
- UYZNXKLDFOYJGI-UHFFFAOYSA-N ethyl 2-[3-[3-[(4-heptyl-2-methyl-3,5-dioxo-1,2,4-triazin-6-yl)amino]propyl]phenyl]sulfanyl-2-methylpropanoate Chemical compound CN1C(=O)N(CCCCCCC)C(=O)C(NCCCC=2C=C(SC(C)(C)C(=O)OCC)C=CC=2)=N1 UYZNXKLDFOYJGI-UHFFFAOYSA-N 0.000 claims 1
- QRXCEVCPODGWKM-UHFFFAOYSA-N ethyl 2-[3-[3-[(4-heptyl-2-methyl-3,5-dioxo-1,2,4-triazin-6-yl)oxy]propyl]phenoxy]-2-methylpropanoate Chemical compound CN1C(=O)N(CCCCCCC)C(=O)C(OCCCC=2C=C(OC(C)(C)C(=O)OCC)C=CC=2)=N1 QRXCEVCPODGWKM-UHFFFAOYSA-N 0.000 claims 1
- DVJHAPROFZBEKR-UHFFFAOYSA-N ethyl 2-[3-[4-[(2,4-diheptyl-3,5-dioxo-1,2,4-triazin-6-yl)amino]butyl]phenyl]sulfanyl-2-methylpropanoate Chemical compound O=C1N(CCCCCCC)C(=O)N(CCCCCCC)N=C1NCCCCC1=CC=CC(SC(C)(C)C(=O)OCC)=C1 DVJHAPROFZBEKR-UHFFFAOYSA-N 0.000 claims 1
- XBNJILZXBIGFFF-UHFFFAOYSA-N ethyl 2-[3-[4-[(2-heptyl-4-methyl-3,5-dioxo-1,2,4-triazin-6-yl)amino]butyl]phenyl]sulfanyl-2-methylpropanoate Chemical compound O=C1N(C)C(=O)N(CCCCCCC)N=C1NCCCCC1=CC=CC(SC(C)(C)C(=O)OCC)=C1 XBNJILZXBIGFFF-UHFFFAOYSA-N 0.000 claims 1
- NSJSMUMMLHIFIX-UHFFFAOYSA-N ethyl 2-[3-[5-[(2-heptyl-4-methyl-3,5-dioxo-1,2,4-triazin-6-yl)oxy]pentyl]phenoxy]-2-methylpropanoate Chemical compound O=C1N(C)C(=O)N(CCCCCCC)N=C1OCCCCCC1=CC=CC(OC(C)(C)C(=O)OCC)=C1 NSJSMUMMLHIFIX-UHFFFAOYSA-N 0.000 claims 1
- HUBDFXZWTWIYEL-UHFFFAOYSA-N ethyl 2-[3-[5-[(4-butyl-2-methyl-3,5-dioxo-1,2,4-triazin-6-yl)oxy]pentyl]phenoxy]-2-methylpropanoate Chemical compound CN1C(=O)N(CCCC)C(=O)C(OCCCCCC=2C=C(OC(C)(C)C(=O)OCC)C=CC=2)=N1 HUBDFXZWTWIYEL-UHFFFAOYSA-N 0.000 claims 1
- LWRVCJUEGOSPMX-UHFFFAOYSA-N ethyl 2-[3-[5-[[4-butyl-3,5-dioxo-2-(4,4,4-trifluorobutyl)-1,2,4-triazin-6-yl]oxy]pentyl]phenoxy]-2-methylpropanoate Chemical compound FC(F)(F)CCCN1C(=O)N(CCCC)C(=O)C(OCCCCCC=2C=C(OC(C)(C)C(=O)OCC)C=CC=2)=N1 LWRVCJUEGOSPMX-UHFFFAOYSA-N 0.000 claims 1
- LBXLCYXNXBNWBZ-UHFFFAOYSA-N ethyl 2-[4-[2-[[4-heptyl-3,5-dioxo-2-(4,4,4-trifluorobutyl)-1,2,4-triazin-6-yl]amino]ethyl]phenoxy]-2-methylpropanoate Chemical compound FC(F)(F)CCCN1C(=O)N(CCCCCCC)C(=O)C(NCCC=2C=CC(OC(C)(C)C(=O)OCC)=CC=2)=N1 LBXLCYXNXBNWBZ-UHFFFAOYSA-N 0.000 claims 1
- YMGOKQCJHJMVQY-UHFFFAOYSA-N ethyl 2-methyl-2-[3-[2-[[2-methyl-3,5-dioxo-4-(4,4,4-trifluorobutyl)-1,2,4-triazin-6-yl]oxy]ethyl]phenoxy]propanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=CC(CCOC=2C(N(CCCC(F)(F)F)C(=O)N(C)N=2)=O)=C1 YMGOKQCJHJMVQY-UHFFFAOYSA-N 0.000 claims 1
- OMUIVKCICKCDMS-UHFFFAOYSA-N ethyl 2-methyl-2-[3-[5-[[2-methyl-3,5-dioxo-4-(4,4,4-trifluorobutyl)-1,2,4-triazin-6-yl]oxy]pentyl]phenoxy]propanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=CC(CCCCCOC=2C(N(CCCC(F)(F)F)C(=O)N(C)N=2)=O)=C1 OMUIVKCICKCDMS-UHFFFAOYSA-N 0.000 claims 1
- AYTQKCWIWLSTKW-UHFFFAOYSA-N ethyl 2-methyl-2-[4-[2-[[4-methyl-3,5-dioxo-2-(4,4,4-trifluorobutyl)-1,2,4-triazin-6-yl]amino]ethyl]phenoxy]propanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1CCNC1=NN(CCCC(F)(F)F)C(=O)N(C)C1=O AYTQKCWIWLSTKW-UHFFFAOYSA-N 0.000 claims 1
- KMOMXZOLYMQEGD-UHFFFAOYSA-N ethyl 2-methyl-2-[4-[2-[[4-methyl-3,5-dioxo-2-(4,4,4-trifluorobutyl)-1,2,4-triazin-6-yl]oxy]ethyl]phenoxy]propanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1CCOC1=NN(CCCC(F)(F)F)C(=O)N(C)C1=O KMOMXZOLYMQEGD-UHFFFAOYSA-N 0.000 claims 1
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- 150000001720 carbohydrates Chemical class 0.000 description 1
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- 208000016097 disease of metabolism Diseases 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 230000037353 metabolic pathway Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 102000006255 nuclear receptors Human genes 0.000 description 1
- 108020004017 nuclear receptors Proteins 0.000 description 1
- 230000036581 peripheral resistance Effects 0.000 description 1
- 210000002824 peroxisome Anatomy 0.000 description 1
- 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members 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
- C07D253/075—Two hetero atoms, in positions 3 and 5
-
- 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
- A61K31/66—Phosphorus compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- A61P39/00—General protective or antinoxious 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Dermatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Emergency Medicine (AREA)
- Vascular Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Urology & Nephrology (AREA)
- Immunology (AREA)
- Toxicology (AREA)
- Cardiology (AREA)
- Endocrinology (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Liquid Crystal Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0502152A FR2882750B1 (fr) | 2005-03-03 | 2005-03-03 | Derives de 1,2,4-triazines, leur preparation et leur application en therapeutique humaine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200707730B true ZA200707730B (en) | 2008-05-28 |
Family
ID=35116027
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200707730A ZA200707730B (en) | 2005-03-03 | 2007-09-10 | 1,2,4-triazine derivatives, preparation and use thereof in human therapy |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US7713971B2 (de) |
| EP (1) | EP1856065B1 (de) |
| JP (1) | JP5269420B2 (de) |
| KR (1) | KR20070112230A (de) |
| CN (1) | CN101155790A (de) |
| AR (1) | AR053155A1 (de) |
| AT (1) | ATE448211T1 (de) |
| AU (1) | AU2006219802A1 (de) |
| BR (1) | BRPI0607567A2 (de) |
| CA (1) | CA2599848A1 (de) |
| CR (1) | CR9366A (de) |
| DE (1) | DE602006010337D1 (de) |
| ES (1) | ES2336823T3 (de) |
| FR (1) | FR2882750B1 (de) |
| IL (1) | IL185586A0 (de) |
| MA (1) | MA29343B1 (de) |
| MX (1) | MX2007010787A (de) |
| MY (1) | MY140662A (de) |
| NI (1) | NI200700224A (de) |
| NO (1) | NO20074881L (de) |
| PL (1) | PL1856065T3 (de) |
| PT (1) | PT1856065E (de) |
| RU (1) | RU2007136027A (de) |
| TN (1) | TNSN07335A1 (de) |
| TW (1) | TW200643016A (de) |
| WO (1) | WO2006092507A1 (de) |
| ZA (1) | ZA200707730B (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2736229C (en) * | 2008-09-05 | 2015-06-09 | Acucela Inc. | Sulfur-linked compounds for treating opthalmic diseases and disorders |
| JP2013538215A (ja) | 2010-08-31 | 2013-10-10 | エスエヌユー アールアンドディービー ファウンデーション | ＰＰＡＲδアゴニストの胎児再プログラミング用途 |
| JP6814730B2 (ja) * | 2014-09-05 | 2021-01-20 | ジェネンテック， インコーポレイテッド | 治療用化合物およびその使用 |
| TWI840423B (zh) * | 2018-10-12 | 2024-05-01 | 美商拓臻股份有限公司 | 甲狀腺素受體β促效劑化合物 |
| CN111320609A (zh) | 2018-12-13 | 2020-06-23 | 拓臻股份有限公司 | 一种THRβ受体激动剂化合物及其制备方法和用途 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2707294B1 (fr) * | 1993-07-06 | 1995-09-29 | Pf Medicament | Nouveaux dérivés de la 3,5-dioxo-(2H,4H)-1,2,4-triazine, leur préparation et leur application en thérapeutique humaine. |
| UA82048C2 (uk) * | 2000-11-10 | 2008-03-11 | Эли Лилли Энд Компани | Агоністи альфа-рецепторів, активованих проліфератором пероксисом |
| GB0113233D0 (en) * | 2001-05-31 | 2001-07-25 | Glaxo Group Ltd | Chemical compounds |
| FR2866339B1 (fr) * | 2004-02-18 | 2006-05-05 | Pf Medicament | Derives de 1,2,4-triazines, leur preparation et leur application en therapeutique humaine |
-
2005
- 2005-03-03 FR FR0502152A patent/FR2882750B1/fr not_active Expired - Fee Related
-
2006
- 2006-03-02 WO PCT/FR2006/000469 patent/WO2006092507A1/fr active Application Filing
- 2006-03-02 RU RU2007136027/04A patent/RU2007136027A/ru not_active Application Discontinuation
- 2006-03-02 ES ES06726008T patent/ES2336823T3/es active Active
- 2006-03-02 CN CNA2006800114913A patent/CN101155790A/zh active Pending
- 2006-03-02 PL PL06726008T patent/PL1856065T3/pl unknown
- 2006-03-02 BR BRPI0607567-3A patent/BRPI0607567A2/pt not_active IP Right Cessation
- 2006-03-02 CA CA002599848A patent/CA2599848A1/fr not_active Abandoned
- 2006-03-02 JP JP2007557542A patent/JP5269420B2/ja not_active Expired - Fee Related
- 2006-03-02 DE DE602006010337T patent/DE602006010337D1/de active Active
- 2006-03-02 EP EP06726008A patent/EP1856065B1/de active Active
- 2006-03-02 KR KR1020077022414A patent/KR20070112230A/ko active IP Right Grant
- 2006-03-02 AT AT06726008T patent/ATE448211T1/de not_active IP Right Cessation
- 2006-03-02 PT PT06726008T patent/PT1856065E/pt unknown
- 2006-03-02 US US11/885,630 patent/US7713971B2/en not_active Expired - Fee Related
- 2006-03-02 AR ARP060100797A patent/AR053155A1/es unknown
- 2006-03-02 TW TW095107034A patent/TW200643016A/zh unknown
- 2006-03-02 AU AU2006219802A patent/AU2006219802A1/en not_active Abandoned
- 2006-03-02 MX MX2007010787A patent/MX2007010787A/es active IP Right Grant
- 2006-03-03 MY MYPI20060914A patent/MY140662A/en unknown
-
2007
- 2007-08-29 IL IL185586A patent/IL185586A0/en unknown
- 2007-08-30 NI NI200700224A patent/NI200700224A/es unknown
- 2007-08-31 TN TNP2007000335A patent/TNSN07335A1/fr unknown
- 2007-09-04 CR CR9366A patent/CR9366A/es not_active Application Discontinuation
- 2007-09-10 ZA ZA200707730A patent/ZA200707730B/en unknown
- 2007-09-25 NO NO20074881A patent/NO20074881L/no not_active Application Discontinuation
- 2007-09-25 MA MA30243A patent/MA29343B1/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006092507A8 (fr) | 2007-11-01 |
| BRPI0607567A2 (pt) | 2011-10-18 |
| CR9366A (es) | 2008-02-12 |
| CA2599848A1 (fr) | 2006-09-08 |
| WO2006092507A1 (fr) | 2006-09-08 |
| NI200700224A (es) | 2008-03-27 |
| US20080167313A1 (en) | 2008-07-10 |
| KR20070112230A (ko) | 2007-11-22 |
| MA29343B1 (fr) | 2008-03-03 |
| ES2336823T3 (es) | 2010-04-16 |
| PL1856065T3 (pl) | 2010-04-30 |
| AU2006219802A1 (en) | 2006-09-08 |
| PT1856065E (pt) | 2010-02-10 |
| EP1856065B1 (de) | 2009-11-11 |
| CN101155790A (zh) | 2008-04-02 |
| US7713971B2 (en) | 2010-05-11 |
| JP5269420B2 (ja) | 2013-08-21 |
| DE602006010337D1 (de) | 2009-12-24 |
| TNSN07335A1 (fr) | 2008-12-31 |
| TW200643016A (en) | 2006-12-16 |
| RU2007136027A (ru) | 2009-04-10 |
| MX2007010787A (es) | 2007-09-25 |
| IL185586A0 (en) | 2008-01-06 |
| FR2882750B1 (fr) | 2007-05-11 |
| MY140662A (en) | 2010-01-15 |
| FR2882750A1 (fr) | 2006-09-08 |
| JP2008531662A (ja) | 2008-08-14 |
| NO20074881L (no) | 2007-11-27 |
| EP1856065A1 (de) | 2007-11-21 |
| AR053155A1 (es) | 2007-04-25 |
| ATE448211T1 (de) | 2009-11-15 |
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