CZ291470B6 - Substituované 3,5-difenyl-1,2,4-triazoly, jejich použití jako léčiv chelatujících kovy a způsob jejich přípravy - Google Patents
Substituované 3,5-difenyl-1,2,4-triazoly, jejich použití jako léčiv chelatujících kovy a způsob jejich přípravy Download PDFInfo
- Publication number
- CZ291470B6 CZ291470B6 CZ19984272A CZ427298A CZ291470B6 CZ 291470 B6 CZ291470 B6 CZ 291470B6 CZ 19984272 A CZ19984272 A CZ 19984272A CZ 427298 A CZ427298 A CZ 427298A CZ 291470 B6 CZ291470 B6 CZ 291470B6
- Authority
- CZ
- Czechia
- Prior art keywords
- carbon atoms
- group
- alkyl
- moiety
- alkoxy
- Prior art date
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 229910052742 iron Inorganic materials 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims description 25
- KPKQWXGFEKRQQA-UHFFFAOYSA-N 3,5-diphenyl-1h-1,2,4-triazole Chemical class C1=CC=CC=C1C1=NNC(C=2C=CC=CC=2)=N1 KPKQWXGFEKRQQA-UHFFFAOYSA-N 0.000 title claims description 16
- 230000008569 process Effects 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 12
- 239000003814 drug Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 59
- 238000011282 treatment Methods 0.000 claims abstract description 14
- 241001465754 Metazoa Species 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 315
- 125000000217 alkyl group Chemical group 0.000 claims description 284
- 125000003545 alkoxy group Chemical group 0.000 claims description 90
- 229910052757 nitrogen Inorganic materials 0.000 claims description 90
- 150000003839 salts Chemical class 0.000 claims description 75
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 71
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 61
- 229910052736 halogen Inorganic materials 0.000 claims description 58
- -1 cyano, hydroxyl Chemical group 0.000 claims description 56
- 150000002367 halogens Chemical class 0.000 claims description 53
- 239000001257 hydrogen Substances 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 52
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 43
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 41
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 40
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 40
- 125000005842 heteroatom Chemical group 0.000 claims description 39
- 150000002431 hydrogen Chemical class 0.000 claims description 38
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 36
- 229910052760 oxygen Inorganic materials 0.000 claims description 33
- 239000001301 oxygen Substances 0.000 claims description 33
- 125000005843 halogen group Chemical group 0.000 claims description 32
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 30
- 125000006413 ring segment Chemical group 0.000 claims description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 29
- 229910052717 sulfur Chemical group 0.000 claims description 29
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 26
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 25
- 239000011593 sulfur Chemical group 0.000 claims description 25
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 24
- 125000001188 haloalkyl group Chemical group 0.000 claims description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims description 18
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 14
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 14
- BOFQWVMAQOTZIW-UHFFFAOYSA-N deferasirox Chemical compound C1=CC(C(=O)O)=CC=C1N1C(C=2C(=CC=CC=2)O)=NC(C=2C(=CC=CC=2)O)=N1 BOFQWVMAQOTZIW-UHFFFAOYSA-N 0.000 claims description 14
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 11
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
- 125000004434 sulfur atom Chemical group 0.000 claims description 11
- 125000003282 alkyl amino group Chemical group 0.000 claims description 10
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 9
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 claims description 8
- 125000001589 carboacyl group Chemical group 0.000 claims description 8
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 230000004962 physiological condition Effects 0.000 claims description 7
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 6
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 6
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 6
- 150000002825 nitriles Chemical class 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- QVNNDPQKBAHUHI-UHFFFAOYSA-N 2-[1-[[4-(diethylamino)phenyl]methyl]-5-(2-hydroxyphenyl)-1,2,4-triazol-3-yl]phenol Chemical compound C1=CC(N(CC)CC)=CC=C1CN1C(C=2C(=CC=CC=2)O)=NC(C=2C(=CC=CC=2)O)=N1 QVNNDPQKBAHUHI-UHFFFAOYSA-N 0.000 claims description 3
- KPUSQGVHCQFTLV-UHFFFAOYSA-N 2-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]-1-(4-methylpiperazin-1-yl)ethanone Chemical compound C1CN(C)CCN1C(=O)CN1C(C=2C(=CC=CC=2)O)=NC(C=2C(=CC=CC=2)O)=N1 KPUSQGVHCQFTLV-UHFFFAOYSA-N 0.000 claims description 3
- RGDZGOMTDMPYDY-UHFFFAOYSA-N 2-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]-N,N-dimethylacetamide Chemical compound CN(C)C(=O)CN1N=C(C=2C(=CC=CC=2)O)N=C1C1=CC=CC=C1O RGDZGOMTDMPYDY-UHFFFAOYSA-N 0.000 claims description 3
- XBEDAENVMHQWQP-UHFFFAOYSA-N 2-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]-N-(2-hydroxyethyl)-N-methylacetamide Chemical compound OCCN(C)C(=O)CN1N=C(C=2C(=CC=CC=2)O)N=C1C1=CC=CC=C1O XBEDAENVMHQWQP-UHFFFAOYSA-N 0.000 claims description 3
- ATLJTHIODMLXBM-UHFFFAOYSA-N 2-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]-N-(2-methoxyethyl)acetamide Chemical compound COCCNC(=O)CN1N=C(C=2C(=CC=CC=2)O)N=C1C1=CC=CC=C1O ATLJTHIODMLXBM-UHFFFAOYSA-N 0.000 claims description 3
- NGJKKFWOJDDGJI-UHFFFAOYSA-N 2-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]-N-[2-(2-hydroxyethoxy)ethyl]acetamide Chemical compound OCCOCCNC(=O)CN1N=C(C=2C(=CC=CC=2)O)N=C1C1=CC=CC=C1O NGJKKFWOJDDGJI-UHFFFAOYSA-N 0.000 claims description 3
- LVBYMPUGOMLQTJ-UHFFFAOYSA-N 2-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]-N-[2-(4-methylpiperazin-1-yl)ethyl]acetamide Chemical compound C1CN(C)CCN1CCNC(=O)CN1C(C=2C(=CC=CC=2)O)=NC(C=2C(=CC=CC=2)O)=N1 LVBYMPUGOMLQTJ-UHFFFAOYSA-N 0.000 claims description 3
- ZFBNGAMIZWACNE-UHFFFAOYSA-N 2-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]-N-[2-(dimethylamino)ethyl]-N-methylacetamide Chemical compound CN(C)CCN(C)C(=O)CN1N=C(C=2C(=CC=CC=2)O)N=C1C1=CC=CC=C1O ZFBNGAMIZWACNE-UHFFFAOYSA-N 0.000 claims description 3
- VHHPZCJPIQOZAG-UHFFFAOYSA-N 2-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]-N-methylacetamide Chemical compound CNC(=O)CN1N=C(C=2C(=CC=CC=2)O)N=C1C1=CC=CC=C1O VHHPZCJPIQOZAG-UHFFFAOYSA-N 0.000 claims description 3
- PDBKAEPAMFPDAZ-UHFFFAOYSA-N 2-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1N1C(C=2C(=CC=CC=2)O)=NC(C=2C(=CC=CC=2)O)=N1 PDBKAEPAMFPDAZ-UHFFFAOYSA-N 0.000 claims description 3
- KFAHBBSYFVWMSB-UHFFFAOYSA-N 2-[5-(2-hydroxyphenyl)-1-(pyridin-3-ylmethyl)-1,2,4-triazol-3-yl]phenol Chemical compound OC1=CC=CC=C1C1=NN(CC=2C=NC=CC=2)C(C=2C(=CC=CC=2)O)=N1 KFAHBBSYFVWMSB-UHFFFAOYSA-N 0.000 claims description 3
- UNESAFKUHWWVAZ-UHFFFAOYSA-N 2-[5-(2-hydroxyphenyl)-1-(pyridin-4-ylmethyl)-1,2,4-triazol-3-yl]phenol Chemical compound OC1=CC=CC=C1C1=NN(CC=2C=CN=CC=2)C(C=2C(=CC=CC=2)O)=N1 UNESAFKUHWWVAZ-UHFFFAOYSA-N 0.000 claims description 3
- AAHAOIYYXCQWNO-UHFFFAOYSA-N 4-[3,5-bis(5-chloro-2-hydroxyphenyl)-1,2,4-triazol-1-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N1C(C=2C(=CC=C(Cl)C=2)O)=NC(C=2C(=CC=C(Cl)C=2)O)=N1 AAHAOIYYXCQWNO-UHFFFAOYSA-N 0.000 claims description 3
- NYMZXCLCWHPTKI-UHFFFAOYSA-N 4-[3,5-bis(5-fluoro-2-hydroxyphenyl)-1,2,4-triazol-1-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N1C(C=2C(=CC=C(F)C=2)O)=NC(C=2C(=CC=C(F)C=2)O)=N1 NYMZXCLCWHPTKI-UHFFFAOYSA-N 0.000 claims description 3
- WFGVLHPUZNSTQY-UHFFFAOYSA-N 4-chloro-2-[5-(5-chloro-2-hydroxyphenyl)-1-(pyridin-2-ylmethyl)-1,2,4-triazol-3-yl]phenol Chemical compound OC1=CC=C(Cl)C=C1C1=NN(CC=2N=CC=CC=2)C(C=2C(=CC=C(Cl)C=2)O)=N1 WFGVLHPUZNSTQY-UHFFFAOYSA-N 0.000 claims description 3
- FCBXFZMLAVTZFK-UHFFFAOYSA-N N-[2-[bis(2-hydroxyethyl)amino]ethyl]-2-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]acetamide Chemical compound OCCN(CCO)CCNC(=O)CN1N=C(C=2C(=CC=CC=2)O)N=C1C1=CC=CC=C1O FCBXFZMLAVTZFK-UHFFFAOYSA-N 0.000 claims description 3
- UFLAPRZZYXBYRM-UHFFFAOYSA-N N-benzyl-2-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]-N-methylacetamide Chemical compound N1=C(C=2C(=CC=CC=2)O)N=C(C=2C(=CC=CC=2)O)N1CC(=O)N(C)CC1=CC=CC=C1 UFLAPRZZYXBYRM-UHFFFAOYSA-N 0.000 claims description 3
- 150000001450 anions Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000002560 nitrile group Chemical group 0.000 claims description 3
- SPFKGZPZHBEFHZ-UHFFFAOYSA-N 2-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]-1-morpholin-4-ylethanone Chemical compound OC1=CC=CC=C1C1=NN(CC(=O)N2CCOCC2)C(C=2C(=CC=CC=2)O)=N1 SPFKGZPZHBEFHZ-UHFFFAOYSA-N 0.000 claims description 2
- ZNUHNRLYJSCKSM-UHFFFAOYSA-N 2-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]-N,N-bis(2-hydroxyethyl)acetamide Chemical compound OCCN(CCO)C(=O)CN1N=C(C=2C(=CC=CC=2)O)N=C1C1=CC=CC=C1O ZNUHNRLYJSCKSM-UHFFFAOYSA-N 0.000 claims description 2
- CTGJRXYZGFEEEW-UHFFFAOYSA-N 2-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]-N-(1,3-dihydroxypropan-2-yl)acetamide Chemical compound OCC(CO)NC(=O)CN1N=C(C=2C(=CC=CC=2)O)N=C1C1=CC=CC=C1O CTGJRXYZGFEEEW-UHFFFAOYSA-N 0.000 claims description 2
- RIOWRULWAPJMLT-UHFFFAOYSA-N 2-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]-N-(2,3-dihydroxypropyl)acetamide Chemical compound OCC(O)CNC(=O)CN1N=C(C=2C(=CC=CC=2)O)N=C1C1=CC=CC=C1O RIOWRULWAPJMLT-UHFFFAOYSA-N 0.000 claims description 2
- DKXUNACJTKLRAK-UHFFFAOYSA-N 2-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]-N-(2-hydroxyethyl)acetamide Chemical compound OCCNC(=O)CN1N=C(C=2C(=CC=CC=2)O)N=C1C1=CC=CC=C1O DKXUNACJTKLRAK-UHFFFAOYSA-N 0.000 claims description 2
- GRAJICIFYWMALU-UHFFFAOYSA-N 2-[5-(2-hydroxyphenyl)-1-[(4-pyrrolidin-1-ylphenyl)methyl]-1,2,4-triazol-3-yl]phenol Chemical compound OC1=CC=CC=C1C1=NN(CC=2C=CC(=CC=2)N2CCCC2)C(C=2C(=CC=CC=2)O)=N1 GRAJICIFYWMALU-UHFFFAOYSA-N 0.000 claims description 2
- HZEHQQRCOFQIFD-UHFFFAOYSA-N 4-[3,5-bis(2-hydroxy-5-methylphenyl)-1,2,4-triazol-1-yl]benzoic acid Chemical compound CC1=CC=C(O)C(C2=NN(C(C=3C(=CC=C(C)C=3)O)=N2)C=2C=CC(=CC=2)C(O)=O)=C1 HZEHQQRCOFQIFD-UHFFFAOYSA-N 0.000 claims description 2
- RSHFRJJEULZHAC-UHFFFAOYSA-N 4-chloro-2-[5-(5-chloro-2-hydroxyphenyl)-1-[[4-(dimethylamino)phenyl]methyl]-1,2,4-triazol-3-yl]phenol Chemical compound C1=CC(N(C)C)=CC=C1CN1C(C=2C(=CC=C(Cl)C=2)O)=NC(C=2C(=CC=C(Cl)C=2)O)=N1 RSHFRJJEULZHAC-UHFFFAOYSA-N 0.000 claims description 2
- GWRITMKEZVPWSA-UHFFFAOYSA-N [4-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(N2C(=NC(=N2)C=2C(=CC=CC=2)O)C=2C(=CC=CC=2)O)C=C1 GWRITMKEZVPWSA-UHFFFAOYSA-N 0.000 claims description 2
- FLLXZXMPTCCCNO-UHFFFAOYSA-N [4-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]phenyl]-morpholin-4-ylmethanone Chemical compound OC1=CC=CC=C1C1=NN(C=2C=CC(=CC=2)C(=O)N2CCOCC2)C(C=2C(=CC=CC=2)O)=N1 FLLXZXMPTCCCNO-UHFFFAOYSA-N 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 2
- JQJJURQBPNASNY-UHFFFAOYSA-N 2-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]-N-(2-morpholin-4-ylethyl)acetamide Chemical compound OC1=CC=CC=C1C1=NN(CC(=O)NCCN2CCOCC2)C(C=2C(=CC=CC=2)O)=N1 JQJJURQBPNASNY-UHFFFAOYSA-N 0.000 claims 1
- QNABQSQCXMUBAY-UHFFFAOYSA-N 2-[3,5-bis(5-chloro-2-hydroxyphenyl)-1,2,4-triazol-1-yl]-N-(2-morpholin-4-ylethyl)acetamide Chemical compound OC1=CC=C(Cl)C=C1C1=NN(CC(=O)NCCN2CCOCC2)C(C=2C(=CC=C(Cl)C=2)O)=N1 QNABQSQCXMUBAY-UHFFFAOYSA-N 0.000 claims 1
- CKUAXEQHGKSLHN-UHFFFAOYSA-N [C].[N] Chemical group [C].[N] CKUAXEQHGKSLHN-UHFFFAOYSA-N 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 206010065973 Iron Overload Diseases 0.000 abstract description 3
- 229910052740 iodine Inorganic materials 0.000 abstract description 3
- 239000002738 chelating agent Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 156
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 81
- 239000000203 mixture Substances 0.000 description 63
- 239000013078 crystal Substances 0.000 description 57
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
- 238000001035 drying Methods 0.000 description 46
- YJKFSPXKSRMHAB-UHFFFAOYSA-N ethyl 2-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]acetate Chemical compound CCOC(=O)CN1N=C(C=2C(=CC=CC=2)O)N=C1C1=CC=CC=C1O YJKFSPXKSRMHAB-UHFFFAOYSA-N 0.000 description 39
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- 239000004480 active ingredient Substances 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
- 239000012044 organic layer Substances 0.000 description 22
- 229910052938 sodium sulfate Inorganic materials 0.000 description 22
- 235000011152 sodium sulphate Nutrition 0.000 description 22
- 238000009835 boiling Methods 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- NSWIROGSZPXREF-UHFFFAOYSA-N 2-(2-hydroxyphenyl)-1,3-benzoxazin-4-one Chemical compound OC1=CC=CC=C1C1=NC(=O)C2=CC=CC=C2O1 NSWIROGSZPXREF-UHFFFAOYSA-N 0.000 description 16
- 239000007858 starting material Substances 0.000 description 16
- 238000001816 cooling Methods 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000003826 tablet Substances 0.000 description 14
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 9
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 9
- 239000008101 lactose Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 239000000454 talc Substances 0.000 description 7
- 229910052623 talc Inorganic materials 0.000 description 7
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- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XBXCNNQPRYLIDE-UHFFFAOYSA-M n-tert-butylcarbamate Chemical compound CC(C)(C)NC([O-])=O XBXCNNQPRYLIDE-UHFFFAOYSA-M 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 229940100692 oral suspension Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001181 organosilyl group Chemical class [SiH3]* 0.000 description 1
- 208000005368 osteomalacia Diseases 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 238000004810 partition chromatography Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000008180 pharmaceutical surfactant Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229940116317 potato starch Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- AMLFJZRZIOZGPW-UHFFFAOYSA-N prop-1-en-1-amine Chemical compound CC=CN AMLFJZRZIOZGPW-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- OHUIBHVOJJTMNX-UHFFFAOYSA-N pyridin-2-ylmethylhydrazine;hydrochloride Chemical compound Cl.NNCC1=CC=CC=N1 OHUIBHVOJJTMNX-UHFFFAOYSA-N 0.000 description 1
- MNRWHUKMYOKCMQ-UHFFFAOYSA-N pyridin-4-ylmethylhydrazine;hydrochloride Chemical compound Cl.NNCC1=CC=NC=C1 MNRWHUKMYOKCMQ-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- 238000005730 ring rearrangement reaction Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 238000000926 separation method Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 208000007056 sickle cell anemia Diseases 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- 229940071536 silver acetate Drugs 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000009747 swallowing Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- A61P39/00—General protective or antinoxious agents
- A61P39/04—Chelating agents
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Toxicology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH159396 | 1996-06-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ427298A3 CZ427298A3 (cs) | 1999-03-17 |
| CZ291470B6 true CZ291470B6 (cs) | 2003-03-12 |
Family
ID=4214048
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ19984272A CZ291470B6 (cs) | 1996-06-25 | 1997-06-24 | Substituované 3,5-difenyl-1,2,4-triazoly, jejich použití jako léčiv chelatujících kovy a způsob jejich přípravy |
Country Status (36)
| Country | Link |
|---|---|
| US (3) | US6465504B1 (OSRAM) |
| EP (1) | EP0914118B1 (OSRAM) |
| JP (1) | JP3541042B2 (OSRAM) |
| KR (1) | KR100616378B1 (OSRAM) |
| CN (1) | CN1146415C (OSRAM) |
| AP (1) | AP1127A (OSRAM) |
| AR (1) | AR007479A1 (OSRAM) |
| AT (1) | ATE226435T1 (OSRAM) |
| AU (1) | AU718037B2 (OSRAM) |
| BG (1) | BG64248B1 (OSRAM) |
| BR (1) | BR9709973A (OSRAM) |
| CA (1) | CA2255951C (OSRAM) |
| CY (2) | CY2429B1 (OSRAM) |
| CZ (1) | CZ291470B6 (OSRAM) |
| DE (3) | DE69716602T2 (OSRAM) |
| DK (1) | DK0914118T3 (OSRAM) |
| ES (1) | ES2187785T3 (OSRAM) |
| FR (1) | FR06C0049I2 (OSRAM) |
| GE (1) | GEP20084355B (OSRAM) |
| HU (1) | HU226232B1 (OSRAM) |
| IL (1) | IL127212A0 (OSRAM) |
| LT (1) | LTC0914118I2 (OSRAM) |
| LU (1) | LU91291I2 (OSRAM) |
| MY (1) | MY129541A (OSRAM) |
| NL (1) | NL300248I2 (OSRAM) |
| NO (3) | NO317180B1 (OSRAM) |
| NZ (1) | NZ333308A (OSRAM) |
| OA (1) | OA10946A (OSRAM) |
| PL (1) | PL194758B1 (OSRAM) |
| PT (1) | PT914118E (OSRAM) |
| RU (1) | RU2208010C2 (OSRAM) |
| SI (1) | SI0914118T1 (OSRAM) |
| SK (1) | SK284319B6 (OSRAM) |
| TR (1) | TR199802693T2 (OSRAM) |
| TW (1) | TW533205B (OSRAM) |
| WO (1) | WO1997049395A1 (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE112008003646T5 (de) | 2008-01-30 | 2011-03-31 | Farmak A.S. | Verfahren zur Herstellung von 4-[3,5-Bis(2-hydroxyphenyl)-[1,2,4]triazol-1-yl]benzoesäure |
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| US6677487B2 (en) | 2001-08-30 | 2004-01-13 | Pharmacia Corporation | α-haloenamine reagents |
| GB0126618D0 (en) | 2001-11-06 | 2002-01-02 | Novartis Ag | Organic compounds |
| ES2192494B1 (es) * | 2002-03-27 | 2005-02-16 | Consejo Superior De Investigaciones Cientificas | Derivados de 1,2,4-triazol con propiedades cannabinoides. |
| US8829198B2 (en) * | 2007-10-31 | 2014-09-09 | Proteotech Inc | Compounds, compositions and methods for the treatment of beta-amyloid diseases and synucleinopathies |
| GB0223978D0 (en) * | 2002-10-15 | 2002-11-20 | Novartis Ag | Organic compound |
| MY142651A (en) * | 2003-03-18 | 2010-12-15 | Merck Sharp & Dohme | Biaryl substituted triazoles as sodium channel blockers |
| US20050008699A1 (en) * | 2003-07-11 | 2005-01-13 | Fred Wehling | Effervescent glucosamine composition |
| EP1694654B1 (en) * | 2003-11-10 | 2011-03-02 | Merck Sharp & Dohme Corp. | Substituted triazoles as sodium channel blockers |
| EP1696917A1 (en) * | 2003-12-19 | 2006-09-06 | Novartis AG | COMBINATION OF (a) N-{5- [4-(4-METHYL-PIPERAZINO-METHYL) -BENZOYLAMIDO] -2METHYLPHENYL]-4-(3-PYRIDYL)-2-PYRIMIDINE-AMINE AND (b) AT LEAST ONE HYPUSINATION INHIBITOR AND THE USE THEREOF |
| GB0408078D0 (en) * | 2004-04-08 | 2004-05-12 | Novartis Ag | Organic compounds |
| WO2005115379A2 (en) * | 2004-05-24 | 2005-12-08 | New York University | Method of treating or preventing pathologic effects of acute increases in hyperglycemia and/or acute increases of free fatty acid flux |
| US9737511B2 (en) * | 2004-05-24 | 2017-08-22 | Geoffrey C. GURTNER | Method of treating or preventing pathologic effects of acute increases in hyperglycemia and/or acute increases of free fatty acid flux |
| PT1843771E (pt) * | 2005-01-28 | 2011-12-02 | Novartis Ag | Uso de pirimidilaminobenzamidas para o tratamento de doenças que respondem à modulação da atividade da cinase tie-2 |
| WO2006084683A1 (en) * | 2005-02-10 | 2006-08-17 | Novartis Ag | Methods for improving drug disposition |
| BRPI0610873A2 (pt) * | 2005-05-31 | 2010-08-03 | Novartis Ag | tratamento de doenças hepáticas em que o ferro desempenhe um papel na patogênese |
| RU2008119410A (ru) * | 2005-10-19 | 2009-11-27 | Новартис АГ (CH) | Диспергируемые таблетки, включающие деферасирокс |
| WO2007051773A1 (en) * | 2005-11-01 | 2007-05-10 | Novartis Ag | Method of scintigraphy |
| US8022091B2 (en) * | 2006-02-03 | 2011-09-20 | Taisho Pharmaceutical Co., Ltd. | Triazole derivative |
| CN101443002B (zh) * | 2006-05-09 | 2012-03-21 | 诺瓦提斯公司 | 包含铁螯合剂和抗肿瘤药的组合及其用途 |
| HRP20140096T1 (hr) * | 2006-05-23 | 2014-02-28 | Novartis Ag | Deferaziroks za lijeäśenje nasljedne hemokromatoze |
| CL2007002026A1 (es) | 2006-07-13 | 2008-06-06 | Los Angeles Biomed Res Inst | Composicion que comprende al menos un compuesto quelante de hierro y al menos un agente antifungico; y metodo para el tratamiento o prevencion de una condicion fungica. |
| CN101500561A (zh) * | 2006-08-04 | 2009-08-05 | 诺瓦提斯公司 | 应用铁螯合剂治疗内分泌功能障碍 |
| RU2339625C2 (ru) * | 2006-11-02 | 2008-11-27 | Российский химико-технологический университет (РХТУ им. Д.И. Менделеева) | ЗАМЕЩЕННЫЕ N-[ω-АЗОЛ-1-ИЛ)АЛКИЛ]БЕНЗОЛСУЛЬФАМИДЫ В КАЧЕСТВЕ СРЕДСТВ С АНТИАГРЕГАЦИОННОЙ АКТИВНОСТЬЮ И СПОСОБЫ ИХ ПОЛУЧЕНИЯ |
| EP1927591A1 (en) * | 2006-11-29 | 2008-06-04 | Novartis AG | Polymorphic Forms of Deferasirox (ICL670) |
| MX2009005619A (es) * | 2006-11-29 | 2009-06-08 | Novartis Ag | Formas poliformicas del deferasirox (icl670a). |
| EP2108013A2 (en) * | 2007-01-29 | 2009-10-14 | Teva Gyógyszergyár Zártköruen Muködo Részvénytársaság | Crystalline forms of deferasirox |
| JP2010526849A (ja) * | 2007-05-14 | 2010-08-05 | ノバルティス アーゲー | 心筋梗塞の治療のための鉄キレート剤の使用 |
| EP1994930A1 (en) * | 2007-05-22 | 2008-11-26 | Novartis AG | Triazol compounds for treating biofilm formation |
| WO2009016359A1 (en) * | 2007-07-27 | 2009-02-05 | Pliva Hrvatska D.O.O. | New forms of deferasirox |
| US20090082412A1 (en) * | 2007-09-26 | 2009-03-26 | Protia, Llc | Deuterium-enriched deferasirox |
| EP2062572A1 (en) | 2007-11-19 | 2009-05-27 | Teva Pharmaceutical Industries Ltd. | Pharmaceutical compositions |
| WO2009106824A2 (en) * | 2008-02-25 | 2009-09-03 | Cipla Limited | Pharmaceutical formulations |
| WO2009111611A2 (en) | 2008-03-05 | 2009-09-11 | Proteotech Inc. | Compounds, compositions and methods for the treatment of islet amyloid polypeptide (iapp) accumulation in diabetes |
| WO2009130604A2 (en) * | 2008-04-21 | 2009-10-29 | Actavis Group Ptc Ehf | Solid state forms of deferasirox salts and process for the preparation thereof |
| WO2009147529A1 (en) * | 2008-06-02 | 2009-12-10 | Actavis Group Ptc Ehf | Substantially pure deferasirox and processes for the preparation thereof |
| TWI488624B (zh) | 2008-09-22 | 2015-06-21 | Nat University Corp Asahikawa Medical College | 鐵螯合劑、其製造方法及鐵離子之定量、捕捉方法 |
| US10098857B2 (en) | 2008-10-10 | 2018-10-16 | The Board Of Trustees Of The Leland Stanford Junior University | Topical and transdermal delivery of HIF-1 modulators to prevent and treat chronic wounds |
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| EP2408804A4 (en) | 2009-03-19 | 2012-10-03 | Los Angeles Biomed Res Inst | VACCINE COMPOSITIONS AND METHODS FOR THE TREATMENT OF MUCORMYCOSIS AND OTHER FUNGAL DISEASES |
| IT1398770B1 (it) * | 2009-07-22 | 2013-03-18 | Bellacchio | Oligonucleotidi attivabili mediante l'appaiamento con sequenze di acidi nucleici e loro uso |
| WO2011021218A2 (en) * | 2009-08-12 | 2011-02-24 | Msn Laboratories Limited | Process for the preparation of 4-[3,5-bis(2-hydroxyphenyl)-1h-1,2,4-triazol-1-yl]-benzoic acid and its amine salts |
| MX2012006434A (es) | 2009-12-07 | 2012-07-30 | Mapi Pharma Ltd | Procesos para la preparacion de deferasirox, y polimorfos de deferasirox. |
| EA201390079A1 (ru) | 2010-07-08 | 2013-09-30 | Рациофарм Гмбх | Пероральная лекарственная форма деферазирокса |
| EP2632907B1 (en) * | 2010-08-25 | 2015-10-14 | Davuluri, Ramamohan Rao | Process for preparing 2-(2-hydroxyphenyl)-benz[1,3]oxazin-4-one and its use for preparing deferasirox |
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| JP5900968B2 (ja) | 2011-01-14 | 2016-04-06 | 株式会社ダステック | 高分子鉄キレート剤 |
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| US8937176B2 (en) | 2011-12-14 | 2015-01-20 | Boehringer Ingelheim International Gmbh | Compounds |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE112008003646T5 (de) | 2008-01-30 | 2011-03-31 | Farmak A.S. | Verfahren zur Herstellung von 4-[3,5-Bis(2-hydroxyphenyl)-[1,2,4]triazol-1-yl]benzoesäure |
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