NO326941B1 - 1,2,4-triazolforbindelse, medikament som omfatter forbindelsen, og anvendelse av forbindelsen for fremstilling av farmasoytisk sammensetning mot sykdom - Google Patents
1,2,4-triazolforbindelse, medikament som omfatter forbindelsen, og anvendelse av forbindelsen for fremstilling av farmasoytisk sammensetning mot sykdom Download PDFInfo
- Publication number
- NO326941B1 NO326941B1 NO20041075A NO20041075A NO326941B1 NO 326941 B1 NO326941 B1 NO 326941B1 NO 20041075 A NO20041075 A NO 20041075A NO 20041075 A NO20041075 A NO 20041075A NO 326941 B1 NO326941 B1 NO 326941B1
- Authority
- NO
- Norway
- Prior art keywords
- group
- ethoxy
- pyridyl
- triazole
- substituted
- Prior art date
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- -1 1,2,4-triazole compound Chemical class 0.000 title claims description 60
- 150000001875 compounds Chemical class 0.000 title claims description 35
- 238000002360 preparation method Methods 0.000 title claims description 21
- 239000003814 drug Substances 0.000 title claims description 9
- 229940079593 drug Drugs 0.000 title claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 title claims 3
- 201000010099 disease Diseases 0.000 title description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical group [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 239000002255 antigout agent Substances 0.000 claims description 2
- 229960002708 antigout preparations Drugs 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical group N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 claims 1
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- 201000001431 Hyperuricemia Diseases 0.000 description 17
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- 229940116269 uric acid Drugs 0.000 description 15
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- 238000006243 chemical reaction Methods 0.000 description 10
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- 235000019341 magnesium sulphate Nutrition 0.000 description 10
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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- 230000002401 inhibitory effect Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 210000002966 serum Anatomy 0.000 description 6
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- UBVZQGOVTLIHLH-UHFFFAOYSA-N 4-[5-pyridin-4-yl-1h-[1,2,4]triazol-3-yl]-pyridine-2-carbonitrile Chemical compound C1=NC(C#N)=CC(C=2N=C(NN=2)C=2C=CN=CC=2)=C1 UBVZQGOVTLIHLH-UHFFFAOYSA-N 0.000 description 4
- 238000002651 drug therapy Methods 0.000 description 4
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
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- 229920000609 methyl cellulose Polymers 0.000 description 3
- 239000001923 methylcellulose Substances 0.000 description 3
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 description 2
- PPDYFTPCRSZNRD-UHFFFAOYSA-N 2-cyanopyridine-4-carbohydrazide Chemical compound NNC(=O)C1=CC=NC(C#N)=C1 PPDYFTPCRSZNRD-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- QCWTWMJMLSKQCJ-UHFFFAOYSA-N Isonicotinic acid N-oxide Chemical compound OC(=O)C1=CC=[N+]([O-])C=C1 QCWTWMJMLSKQCJ-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 229960003459 allopurinol Drugs 0.000 description 2
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- 150000002463 imidates Chemical class 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
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- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- 239000003064 xanthine oxidase inhibitor Substances 0.000 description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
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- RMVTUWYVZAEPCE-UHFFFAOYSA-N 2-(2-methoxyethoxy)-5-[5-(2-methylpyridin-4-yl)-1h-1,2,4-triazol-3-yl]benzonitrile Chemical compound C1=C(C#N)C(OCCOC)=CC=C1C1=NC(C=2C=C(C)N=CC=2)=NN1 RMVTUWYVZAEPCE-UHFFFAOYSA-N 0.000 description 1
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- GMHOFAKYMWZDBN-UHFFFAOYSA-N 2-(2-methylpropoxy)-5-(5-pyridin-4-yl-1h-1,2,4-triazol-3-yl)benzonitrile Chemical compound C1=C(C#N)C(OCC(C)C)=CC=C1C1=NNC(C=2C=CN=CC=2)=N1 GMHOFAKYMWZDBN-UHFFFAOYSA-N 0.000 description 1
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- WSHIQYNFRRPTFT-UHFFFAOYSA-N 2-(3-methylbutoxy)-5-[5-(2-methylpyridin-4-yl)-1h-1,2,4-triazol-3-yl]benzonitrile Chemical compound C1=C(C#N)C(OCCC(C)C)=CC=C1C1=NC(C=2C=C(C)N=CC=2)=NN1 WSHIQYNFRRPTFT-UHFFFAOYSA-N 0.000 description 1
- KGMSNGUDYJDEPR-UHFFFAOYSA-N 2-(cyclopropylmethoxy)-5-[5-(2-methylpyridin-4-yl)-1h-1,2,4-triazol-3-yl]benzonitrile Chemical compound C1=NC(C)=CC(C=2N=C(NN=2)C=2C=C(C(OCC3CC3)=CC=2)C#N)=C1 KGMSNGUDYJDEPR-UHFFFAOYSA-N 0.000 description 1
- XGURUKMNBZWRMS-UHFFFAOYSA-N 2-[(4-methoxyphenyl)methoxy]-5-[5-(2-methylpyridin-4-yl)-1h-1,2,4-triazol-3-yl]benzonitrile Chemical compound C1=CC(OC)=CC=C1COC1=CC=C(C=2NN=C(N=2)C=2C=C(C)N=CC=2)C=C1C#N XGURUKMNBZWRMS-UHFFFAOYSA-N 0.000 description 1
- XZGPWOPYSAJTIB-UHFFFAOYSA-N 2-[2-(2-methoxyethoxy)ethoxy]-5-[5-(2-methylpyridin-4-yl)-1h-1,2,4-triazol-3-yl]benzonitrile Chemical compound C1=C(C#N)C(OCCOCCOC)=CC=C1C1=NNC(C=2C=C(C)N=CC=2)=N1 XZGPWOPYSAJTIB-UHFFFAOYSA-N 0.000 description 1
- UDBNVFCQOBDJJD-UHFFFAOYSA-N 2-[3-[4-(2-methylpropoxy)-3-nitrophenyl]-1h-1,2,4-triazol-5-yl]pyridine Chemical compound C1=C([N+]([O-])=O)C(OCC(C)C)=CC=C1C1=NC(C=2N=CC=CC=2)=NN1 UDBNVFCQOBDJJD-UHFFFAOYSA-N 0.000 description 1
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 1
- UGTYPRAMKKJBJA-UHFFFAOYSA-N 2-chloro-4-[3-(2-methylpyridin-4-yl)-1h-1,2,4-triazol-5-yl]pyridine Chemical compound C1=NC(C)=CC(C=2NN=C(N=2)C=2C=C(Cl)N=CC=2)=C1 UGTYPRAMKKJBJA-UHFFFAOYSA-N 0.000 description 1
- NZWIZGDFGDJSAD-UHFFFAOYSA-N 2-chloro-4-[3-[4-(2-methylpropoxy)-3-nitrophenyl]-1h-1,2,4-triazol-5-yl]pyridine Chemical compound C1=C([N+]([O-])=O)C(OCC(C)C)=CC=C1C1=NNC(C=2C=C(Cl)N=CC=2)=N1 NZWIZGDFGDJSAD-UHFFFAOYSA-N 0.000 description 1
- 125000006012 2-chloroethoxy group Chemical group 0.000 description 1
- WXGHWQUKMJZWGV-UHFFFAOYSA-N 2-methoxy-5-[5-(2-methylpyridin-4-yl)-1h-1,2,4-triazol-3-yl]benzonitrile Chemical compound C1=C(C#N)C(OC)=CC=C1C1=NC(C=2C=C(C)N=CC=2)=NN1 WXGHWQUKMJZWGV-UHFFFAOYSA-N 0.000 description 1
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- DJAMIUAGKWATKH-UHFFFAOYSA-N 2-methyl-4-[3-[3-nitro-4-(oxan-2-ylmethoxy)phenyl]-1h-1,2,4-triazol-5-yl]pyridine Chemical compound C1=NC(C)=CC(C=2NN=C(N=2)C=2C=C(C(OCC3OCCCC3)=CC=2)[N+]([O-])=O)=C1 DJAMIUAGKWATKH-UHFFFAOYSA-N 0.000 description 1
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- GJUQULNTUDILRT-UHFFFAOYSA-N 4-[3-[4-(2-methylpropoxy)-3-nitrophenyl]-1h-1,2,4-triazol-5-yl]pyridine Chemical compound C1=C([N+]([O-])=O)C(OCC(C)C)=CC=C1C1=NNC(C=2C=CN=CC=2)=N1 GJUQULNTUDILRT-UHFFFAOYSA-N 0.000 description 1
- XBLPHYSLHRGMNW-UHFFFAOYSA-N 4-chloro-3-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC(C#N)=CC=C1Cl XBLPHYSLHRGMNW-UHFFFAOYSA-N 0.000 description 1
- NKJIFDNZPGLLSH-UHFFFAOYSA-N 4-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC=C(C#N)C=C1 NKJIFDNZPGLLSH-UHFFFAOYSA-N 0.000 description 1
- CBTKOYZHXSJBMX-UHFFFAOYSA-N 5-[5-(2-methylpyridin-4-yl)-1h-1,2,4-triazol-3-yl]-2-prop-2-ynoxybenzonitrile Chemical compound C1=NC(C)=CC(C=2N=C(NN=2)C=2C=C(C(OCC#C)=CC=2)C#N)=C1 CBTKOYZHXSJBMX-UHFFFAOYSA-N 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- GKQLYSROISKDLL-UHFFFAOYSA-N EEDQ Chemical compound C1=CC=C2N(C(=O)OCC)C(OCC)C=CC2=C1 GKQLYSROISKDLL-UHFFFAOYSA-N 0.000 description 1
- 208000010201 Exanthema Diseases 0.000 description 1
- 206010057249 Phagocytosis Diseases 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 206010062237 Renal impairment Diseases 0.000 description 1
- 229940123769 Xanthine oxidase inhibitor Drugs 0.000 description 1
- RLPWDBOJAHPKJY-UHFFFAOYSA-N [3-[4-(2-methylpropoxy)-3-nitrophenyl]-5-(2-methylpyridin-4-yl)-1,2,4-triazol-1-yl]methyl 2,2-dimethylpropanoate Chemical compound C1=C([N+]([O-])=O)C(OCC(C)C)=CC=C1C1=NN(COC(=O)C(C)(C)C)C(C=2C=C(C)N=CC=2)=N1 RLPWDBOJAHPKJY-UHFFFAOYSA-N 0.000 description 1
- 230000003113 alkalizing effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Chemical class 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229960002529 benzbromarone Drugs 0.000 description 1
- WHQCHUCQKNIQEC-UHFFFAOYSA-N benzbromarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC(Br)=C(O)C(Br)=C1 WHQCHUCQKNIQEC-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000035605 chemotaxis Effects 0.000 description 1
- GGRHYQCXXYLUTL-UHFFFAOYSA-N chloromethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCCl GGRHYQCXXYLUTL-UHFFFAOYSA-N 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 229960001338 colchicine Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 201000005884 exanthem Diseases 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 208000006454 hepatitis Diseases 0.000 description 1
- 231100000283 hepatitis Toxicity 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- XSGNXRNOZMUURC-UHFFFAOYSA-N methyl 1-oxidopyridin-1-ium-4-carboxylate Chemical compound COC(=O)C1=CC=[N+]([O-])C=C1 XSGNXRNOZMUURC-UHFFFAOYSA-N 0.000 description 1
- ORVHMLCJEKDDAX-UHFFFAOYSA-N methyl 2-cyanopyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC(C#N)=C1 ORVHMLCJEKDDAX-UHFFFAOYSA-N 0.000 description 1
- LANVNPIQGZTJQC-UHFFFAOYSA-N n-(2-methylpropyl)-4-[5-(2-methylpyridin-4-yl)-1h-1,2,4-triazol-3-yl]-2-nitroaniline Chemical compound C1=C([N+]([O-])=O)C(NCC(C)C)=CC=C1C1=NNC(C=2C=C(C)N=CC=2)=N1 LANVNPIQGZTJQC-UHFFFAOYSA-N 0.000 description 1
- 210000000440 neutrophil Anatomy 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- HXNFUBHNUDHIGC-UHFFFAOYSA-N oxypurinol Chemical compound O=C1NC(=O)N=C2NNC=C21 HXNFUBHNUDHIGC-UHFFFAOYSA-N 0.000 description 1
- 230000008782 phagocytosis Effects 0.000 description 1
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- FJWLWIRHZOHPIY-UHFFFAOYSA-N potassium;hydroiodide Chemical compound [K].I FJWLWIRHZOHPIY-UHFFFAOYSA-N 0.000 description 1
- 238000009117 preventive therapy Methods 0.000 description 1
- 229960003081 probenecid Drugs 0.000 description 1
- DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Chemical class 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000002294 steroidal antiinflammatory agent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- MBGGBVCUIVRRBF-UHFFFAOYSA-N sulfinpyrazone Chemical compound O=C1N(C=2C=CC=CC=2)N(C=2C=CC=CC=2)C(=O)C1CCS(=O)C1=CC=CC=C1 MBGGBVCUIVRRBF-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07D413/10—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 aromatic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric 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
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D401/14—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 three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002017825 | 2002-01-28 | ||
| PCT/JP2002/012662 WO2003064410A1 (fr) | 2002-01-28 | 2002-12-03 | Nouveau compose 1,2,4-triazole |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20041075L NO20041075L (no) | 2004-03-15 |
| NO326941B1 true NO326941B1 (no) | 2009-03-16 |
Family
ID=27653386
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20041075A NO326941B1 (no) | 2002-01-28 | 2004-03-15 | 1,2,4-triazolforbindelse, medikament som omfatter forbindelsen, og anvendelse av forbindelsen for fremstilling av farmasoytisk sammensetning mot sykdom |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US7074816B2 (ja) |
| EP (1) | EP1471065B1 (ja) |
| JP (1) | JP3600832B2 (ja) |
| CN (1) | CN1561340B (ja) |
| AR (1) | AR042602A1 (ja) |
| AT (1) | ATE387438T1 (ja) |
| AU (1) | AU2002349754B2 (ja) |
| BR (1) | BRPI0212775B8 (ja) |
| CA (1) | CA2462132C (ja) |
| DE (1) | DE60225341T2 (ja) |
| DK (1) | DK1471065T3 (ja) |
| ES (1) | ES2300486T3 (ja) |
| HK (1) | HK1067132A1 (ja) |
| MX (1) | MXPA04004037A (ja) |
| NO (1) | NO326941B1 (ja) |
| NZ (1) | NZ531673A (ja) |
| PL (1) | PL208260B1 (ja) |
| PT (1) | PT1471065E (ja) |
| RU (1) | RU2293733C2 (ja) |
| TW (1) | TWI257926B (ja) |
| WO (1) | WO2003064410A1 (ja) |
| ZA (1) | ZA200401777B (ja) |
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20060037373A (ko) * | 2003-07-24 | 2006-05-03 | 가부시키가이샤 후지야쿠힝 | 1,2,4-트리아졸 화합물의 제조 방법 및 그 중간체 |
| US20060189811A1 (en) * | 2004-07-23 | 2006-08-24 | Fujiyakuhin Co., Ltd. | Process for producing 1,2,4-triazole compound and intermediate therefor |
| WO2006121995A2 (en) | 2005-05-09 | 2006-11-16 | Tap Pharmaceutical Products, Inc. | Methods for treating nephrolithiasis |
| EP1940397A4 (en) * | 2005-08-03 | 2010-01-20 | Takeda Pharmaceuticals North A | METHOD FOR TREATING HYPERTONIA |
| KR20080066938A (ko) * | 2005-10-07 | 2008-07-17 | 깃세이 야쿠힌 고교 가부시키가이샤 | 질소 함유 복소환 화합물 및 그것을 함유하는 의약 조성물 |
| KR20140037954A (ko) * | 2006-06-22 | 2014-03-27 | 닛뽕 케미파 가부시키가이샤 | 항암제 내성 극복제 |
| JP5110536B2 (ja) * | 2006-07-19 | 2012-12-26 | 学校法人日本医科大学 | 筋萎縮性側索硬化症治療薬 |
| KR20160031040A (ko) * | 2006-11-13 | 2016-03-21 | 다케다 파마슈티칼스 유에스에이, 인코포레이티드 | 크산틴 옥시도리덕타아제 억제제를 사용하여 신장 기능을 보존하는 방법 |
| US20090124623A1 (en) * | 2006-11-13 | 2009-05-14 | Christopher Lademacher | Methods for preserving and/or increasing renal function using xanthine oxidoreductase inhibitors |
| JP2010516691A (ja) * | 2007-01-19 | 2010-05-20 | タケダ ファーマシーティカルズ ノース アメリカ，アイエヌシー． | 抗炎症剤及びキサンチン酸化還元酵素阻害剤を用いて痛風の突発を抑え、又はその数を減少させる方法 |
| JO2784B1 (en) * | 2007-10-18 | 2014-03-15 | شركة جانسين فارماسوتيكا ان. في | 5,3,1 - Triazole substitute derivative |
| DK2217577T3 (da) | 2007-11-27 | 2014-10-20 | Ardea Biosciences Inc | Hidtil ukendte forbindelser og præparater og fremgangsmåder til anvendelse deraf |
| EP2165705A1 (en) | 2008-09-18 | 2010-03-24 | Centre National de la Recherche Scientifique (CNRS) | Use of a compound capable of reducing the uric acid level for the prevention and/or the treatment of lung inflammation and fibrosis |
| US20100311756A1 (en) * | 2009-01-22 | 2010-12-09 | Takeda Pharmaceuticals North America, Inc. | Methods for delaying the progression of at least one of cardiac hypertrophy, cardiac remodeling or left ventricular function or the onset of heart failure in subjects in need of treatment thereof |
| RU2013109380A (ru) | 2010-09-10 | 2014-10-20 | Такеда Фармасьютикалс Ю.С.А.,Инк. | Способ сопутствующей терапии с применением теофиллина и фебуксостата |
| WO2012060308A1 (ja) * | 2010-11-01 | 2012-05-10 | 株式会社 三和化学研究所 | 腎機能障害の予防又は治療に用いる医薬 |
| RU2538964C1 (ru) | 2010-12-17 | 2015-01-10 | Мицубиси Танабе Фарма Корпорейшн | Соединение с последовательной арициклической структурой, обладающее активностью ингибирования ацилкофермента а: диацилглицеринацилтрансферазы (dgat1) |
| WO2012118485A1 (en) | 2011-03-01 | 2012-09-07 | Empire Technology Development Llc | Temperature controlled variable reflectivity coatings |
| RU2476428C1 (ru) * | 2011-09-01 | 2013-02-27 | Государственное образовательное учреждение высшего профессионального образования "Южно-Российский государственный технический университет (Новочеркасский политехнический институт)" | Способ получения дигидрохлорида 5-амино-3-аминометил-1,2,4-триазола |
| ES2690315T3 (es) | 2012-06-15 | 2018-11-20 | Mitsubishi Tanabe Pharma Corporation | Compuestos de imidazol y triazol como inhibidores de DGAT-1 |
| CN104411700B (zh) * | 2012-07-25 | 2016-06-15 | 株式会社富士药品 | 4-[5-(吡啶-4-基)-1h-1,2,4-三唑-3-基]吡啶-2-腈的多晶型及其制造方法 |
| BR112014032229B1 (pt) * | 2012-07-25 | 2021-02-09 | Fujiyakuhin Co., Ltd. | método para produzir 4-[5-(piridin-4-il)-1h-1,2,4-triazol-3- il]piridina-2-carbonitrila |
| CN103724329B (zh) * | 2013-12-23 | 2015-02-18 | 济南百诺医药科技开发有限公司 | 4-[5-(吡啶-4-基)-1h-[1,2,4]三唑-3-基]吡啶-2-甲腈的制备方法 |
| CN104042577B (zh) * | 2014-06-13 | 2016-08-24 | 安徽省逸欣铭医药科技有限公司 | 一种稳定的托匹司他片及其制备方法 |
| CN105315260A (zh) * | 2014-07-29 | 2016-02-10 | 北京海步医药科技股份有限公司 | 一种托布司他一水合物晶型及其制备方法 |
| CN105367490B (zh) * | 2014-08-18 | 2019-01-04 | 上海医药工业研究院 | 合成托吡司他的新中间体及其制备方法 |
| CN105348264B (zh) * | 2014-08-18 | 2018-01-16 | 上海医药工业研究院 | 一种托吡司他的合成方法 |
| CN104151297B (zh) * | 2014-08-27 | 2016-03-16 | 王庆本 | 4-[5-(吡啶-4-基)-1h-[1，2，4]三唑-3-基]吡啶-2-甲腈的制备方法 |
| JP6684264B2 (ja) * | 2015-02-17 | 2020-04-22 | 株式会社三和化学研究所 | 心不全の予防又は治療のための医薬 |
| JP6891108B2 (ja) | 2015-02-24 | 2021-06-18 | 国立大学法人鳥取大学 | 認知症の予防及び／又は治療のための医薬 |
| CN107531677A (zh) * | 2015-02-25 | 2018-01-02 | 法尔玛赞公司 | 用于制备托匹司他及其中间体的方法 |
| CN105693699B (zh) * | 2015-03-30 | 2019-06-18 | 苏州晶云药物科技股份有限公司 | 托吡司他的晶型及其制备方法 |
| CN104910068B (zh) * | 2015-04-24 | 2017-07-14 | 南京医科大学 | 一种2‑氰基异烟酸酰肼1.5对甲苯磺酸盐的合成方法 |
| CN106279111A (zh) * | 2015-05-12 | 2017-01-04 | 北京济美堂医药研究有限公司 | 一种精制托吡司他的新方法 |
| CN104961730B (zh) * | 2015-06-18 | 2017-05-17 | 山东金城医药化工股份有限公司 | 托吡司他新晶型及其制备方法 |
| CN105130958B (zh) * | 2015-08-31 | 2017-10-31 | 济南康和医药科技有限公司 | 5‑(2‑氰基4‑吡啶基)‑3‑(4‑吡啶基)‑1,2,4‑三唑的制备工艺 |
| CN105294656A (zh) * | 2015-10-10 | 2016-02-03 | 大道隆达（北京）医药科技发展有限公司 | 一种托匹司他的制备工艺和方法 |
| CN106336399A (zh) * | 2015-11-03 | 2017-01-18 | 江苏悦兴药业有限公司 | 托匹司他工艺杂质的制备方法 |
| CN105294584A (zh) * | 2015-11-30 | 2016-02-03 | 中国医科大学 | 1-取代苯基-1h-1,2,3-三唑类化合物、制备方法及其用途 |
| CN105399732A (zh) * | 2015-12-07 | 2016-03-16 | 青岛正大海尔制药有限公司 | 一种托匹司他的制备方法 |
| CN106008465A (zh) * | 2016-03-16 | 2016-10-12 | 江苏悦兴药业有限公司 | 一种托匹司他杂质的合成方法 |
| CN108250183A (zh) * | 2016-12-29 | 2018-07-06 | 北京诚济制药有限公司 | 一种高纯度的托匹司他的制备方法 |
| CN109721586B (zh) * | 2017-10-27 | 2021-03-02 | 中国医科大学 | 一种5-苄基-3-吡啶基-1h-1,2,4-三唑类化合物及其制备方法和用途 |
| CN107652271B (zh) * | 2017-11-06 | 2020-06-16 | 上海中拓医药科技有限公司 | 一种托匹司他晶型i的制备方法 |
| CN108017619B (zh) * | 2017-12-06 | 2020-08-11 | 成都惟邦药业有限公司 | 一种托匹司他杂质及其制备方法 |
| CN113354616B (zh) * | 2020-03-05 | 2024-03-26 | 中国医学科学院药物研究所 | 二芳基-1,2,4-三唑类化合物及其制法和药物用途 |
| CN113666909B (zh) * | 2020-05-14 | 2024-07-02 | 鲁南制药集团股份有限公司 | 一种托匹司他的制备方法 |
| CN114773262B (zh) * | 2022-05-19 | 2024-05-07 | 兄弟科技股份有限公司 | 2-氰基-4-吡啶羧酸甲酯的合成方法 |
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| NL7112373A (ja) * | 1970-09-25 | 1972-03-28 | ||
| US3947577A (en) * | 1973-05-21 | 1976-03-30 | Merck & Co., Inc. | Anti-hyperuricemia composition |
| US3963731A (en) * | 1973-05-21 | 1976-06-15 | Merck & Co., Inc. | Pyridyl containing 1-benzenesulfonyl triazoles |
| US3928361A (en) * | 1973-05-21 | 1975-12-23 | Merck & Co Inc | 1-(Sulfamoylphenylalkyl)-3,5-dipyridyl-1,2,4 triazoles |
| US3984558A (en) * | 1973-05-21 | 1976-10-05 | Merck & Co., Inc. | 1,3,5-Trisubstituted-1,2,4-triazole compounds used as bronchodilators |
| US3882134A (en) * | 1973-05-21 | 1975-05-06 | Merck & Co Inc | 1-Substituted-3,5-dipyridyl-1,2,4-triazoles |
| US4104393A (en) * | 1976-04-02 | 1978-08-01 | Merck & Co., Inc. | 1,3,5-Trisubstituted-1,2,4-triazole compounds |
| ES2133312T3 (es) * | 1991-12-05 | 1999-09-16 | Wallac Oy | Quelatos de lantanidos luminiscentes. |
| WO2000024735A1 (en) * | 1998-10-23 | 2000-05-04 | Dow Agrosciences Llc | Insecticidal 1-(substituted pyridyl)-1,2,4-triazoles |
| EP1379525B1 (en) * | 2001-02-21 | 2007-10-10 | Nps Pharmaceuticals, Inc. | Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
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