HUP0400733A2 - Új benzilamino-pirimidinek, alkalmazásuk és ezeket tartalmazó gyógyszerkészítmények - Google Patents
Új benzilamino-pirimidinek, alkalmazásuk és ezeket tartalmazó gyógyszerkészítmények Download PDFInfo
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- HUP0400733A2 HUP0400733A2 HU0400733A HUP0400733A HUP0400733A2 HU P0400733 A2 HUP0400733 A2 HU P0400733A2 HU 0400733 A HU0400733 A HU 0400733A HU P0400733 A HUP0400733 A HU P0400733A HU P0400733 A2 HUP0400733 A2 HU P0400733A2
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- HU
- Hungary
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- group
- atom
- hydrogen atom
- alkyl
- alkoxy
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- XLWNLCSWRLEMJR-UHFFFAOYSA-N n-benzylpyrimidin-2-amine Chemical class C=1C=CC=CC=1CNC1=NC=CC=N1 XLWNLCSWRLEMJR-UHFFFAOYSA-N 0.000 title abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 169
- 150000001875 compounds Chemical class 0.000 claims abstract description 116
- 125000005843 halogen group Chemical group 0.000 claims abstract description 68
- -1 hydroxyl- Chemical group 0.000 claims abstract description 49
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 42
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 37
- 239000011737 fluorine Substances 0.000 claims abstract description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 29
- 239000001257 hydrogen Substances 0.000 claims abstract description 29
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 29
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 27
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 24
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 21
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 20
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 19
- 150000002367 halogens Chemical class 0.000 claims abstract description 19
- 241000589989 Helicobacter Species 0.000 claims abstract description 12
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 10
- 125000002619 bicyclic group Chemical group 0.000 claims abstract description 9
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 90
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 76
- 150000003839 salts Chemical class 0.000 claims description 52
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 50
- 229910052801 chlorine Chemical group 0.000 claims description 26
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 22
- 239000000460 chlorine Chemical group 0.000 claims description 16
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- MJQSRSOTRPMVKB-UHFFFAOYSA-N 5h-imidazo[4,5-c]pyridazine Chemical compound C1=NNC2=NC=NC2=C1 MJQSRSOTRPMVKB-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- HFEDDQUHKFMKJR-UHFFFAOYSA-N 5-chloro-2,6-dimethyl-n-[[4-(3-nitroimidazo[1,2-b]pyridazin-6-yl)oxyphenyl]methyl]pyrimidin-4-amine Chemical compound CC1=NC(C)=C(Cl)C(NCC=2C=CC(OC3=NN4C([N+]([O-])=O)=CN=C4C=C3)=CC=2)=N1 HFEDDQUHKFMKJR-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 32
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 64
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 238000000034 method Methods 0.000 description 25
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- 239000007787 solid Substances 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 239000000741 silica gel Substances 0.000 description 17
- 229910002027 silica gel Inorganic materials 0.000 description 17
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000012071 phase Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000002425 crystallisation Methods 0.000 description 12
- 230000008025 crystallization Effects 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- IJEZMDPWGDWYKJ-UHFFFAOYSA-N 6-chloro-3-nitroimidazo[1,2-b]pyridazine Chemical compound C1=CC(Cl)=NN2C([N+](=O)[O-])=CN=C21 IJEZMDPWGDWYKJ-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 241000590002 Helicobacter pylori Species 0.000 description 8
- BKFCZKYCVQQMCX-UHFFFAOYSA-N 5-chloro-2,6-dimethylpyrimidin-4-amine Chemical compound CC1=NC(C)=C(Cl)C(N)=N1 BKFCZKYCVQQMCX-UHFFFAOYSA-N 0.000 description 7
- ATRJPMXOEPCCSQ-UHFFFAOYSA-N 5-chloro-n-[[3-(cyclopropylmethoxy)-4-phenylmethoxyphenyl]methyl]-2,6-dimethylpyrimidin-4-amine Chemical compound CC1=NC(C)=C(Cl)C(NCC=2C=C(OCC3CC3)C(OCC=3C=CC=CC=3)=CC=2)=N1 ATRJPMXOEPCCSQ-UHFFFAOYSA-N 0.000 description 7
- 229940037467 helicobacter pylori Drugs 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- IUVCFHHAEHNCFT-INIZCTEOSA-N 2-[(1s)-1-[4-amino-3-(3-fluoro-4-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(F)C(OC(C)C)=CC=C1C(C1=C(N)N=CN=C11)=NN1[C@@H](C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC(F)=CC=C2O1 IUVCFHHAEHNCFT-INIZCTEOSA-N 0.000 description 4
- RZIXVOFVPOMNBP-UHFFFAOYSA-N 3-[[(5-chloro-2,6-dimethylpyrimidin-4-yl)amino]methyl]phenol Chemical compound CC1=NC(C)=C(Cl)C(NCC=2C=C(O)C=CC=2)=N1 RZIXVOFVPOMNBP-UHFFFAOYSA-N 0.000 description 4
- NJFVYOVXOXMGCC-UHFFFAOYSA-N 4-[[(5-chloropyrimidin-4-yl)amino]methyl]phenol Chemical compound C1=CC(O)=CC=C1CNC1=NC=NC=C1Cl NJFVYOVXOXMGCC-UHFFFAOYSA-N 0.000 description 4
- OTKTXEOZFISFSX-UHFFFAOYSA-N 5-chloro-2,6-dimethyl-n-[(3-phenylmethoxyphenyl)methyl]pyrimidin-4-amine Chemical compound CC1=NC(C)=C(Cl)C(NCC=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OTKTXEOZFISFSX-UHFFFAOYSA-N 0.000 description 4
- PVPCPAQEXLWVED-UHFFFAOYSA-N 5-chloro-n-[(3-methoxy-4-phenylmethoxyphenyl)methyl]-2,6-dimethylpyrimidin-4-amine Chemical compound C=1C=C(OCC=2C=CC=CC=2)C(OC)=CC=1CNC1=NC(C)=NC(C)=C1Cl PVPCPAQEXLWVED-UHFFFAOYSA-N 0.000 description 4
- GAAMKTZKQZHGBH-UHFFFAOYSA-N 5-chloro-n-[(4-methoxy-3-phenylmethoxyphenyl)methyl]-2,6-dimethylpyrimidin-4-amine Chemical compound C1=C(OCC=2C=CC=CC=2)C(OC)=CC=C1CNC1=NC(C)=NC(C)=C1Cl GAAMKTZKQZHGBH-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 101710122864 Major tegument protein Proteins 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 101710148592 PTS system fructose-like EIIA component Proteins 0.000 description 4
- 101710169713 PTS system fructose-specific EIIA component Proteins 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 101710199973 Tail tube protein Proteins 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229940057995 liquid paraffin Drugs 0.000 description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- KIRDTPFDLJYUQG-UHFFFAOYSA-N 5-chloro-n-[[3-(difluoromethoxy)-4-phenylmethoxyphenyl]methyl]-2,6-dimethylpyrimidin-4-amine Chemical compound CC1=NC(C)=C(Cl)C(NCC=2C=C(OC(F)F)C(OCC=3C=CC=CC=3)=CC=2)=N1 KIRDTPFDLJYUQG-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 108010046334 Urease Proteins 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
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- 238000002844 melting Methods 0.000 description 3
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- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- UYQPSKUPEXAQRJ-UHFFFAOYSA-N 1-(chloromethyl)-4-phenylmethoxybenzene Chemical compound C1=CC(CCl)=CC=C1OCC1=CC=CC=C1 UYQPSKUPEXAQRJ-UHFFFAOYSA-N 0.000 description 2
- WPMDJOHWOGIXQI-UHFFFAOYSA-N 2-(cyclopropylmethoxy)-4-[[(2,6-dimethylpyrimidin-4-yl)amino]methyl]phenol Chemical compound CC1=NC(C)=CC(NCC=2C=C(OCC3CC3)C(O)=CC=2)=N1 WPMDJOHWOGIXQI-UHFFFAOYSA-N 0.000 description 2
- KRCTWDSVGNGCGU-UHFFFAOYSA-N 4-[[(5-chloro-2,6-dimethylpyrimidin-4-yl)amino]methyl]-2-(cyclopropylmethoxy)phenol Chemical compound CC1=NC(C)=C(Cl)C(NCC=2C=C(OCC3CC3)C(O)=CC=2)=N1 KRCTWDSVGNGCGU-UHFFFAOYSA-N 0.000 description 2
- GOFVYDJGHJTQSI-UHFFFAOYSA-N 4-[[(5-chloro-2,6-dimethylpyrimidin-4-yl)amino]methyl]-2-(difluoromethoxy)phenol Chemical compound CC1=NC(C)=C(Cl)C(NCC=2C=C(OC(F)F)C(O)=CC=2)=N1 GOFVYDJGHJTQSI-UHFFFAOYSA-N 0.000 description 2
- KUDRSYXNEIQVBW-UHFFFAOYSA-N 4-[[(5-chloro-2,6-dimethylpyrimidin-4-yl)amino]methyl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC(CNC=2C(=C(C)N=C(C)N=2)Cl)=C1 KUDRSYXNEIQVBW-UHFFFAOYSA-N 0.000 description 2
- LNOXGJSWKWKZBB-UHFFFAOYSA-N 4-[[(5-chloro-2,6-dimethylpyrimidin-4-yl)amino]methyl]phenol Chemical compound CC1=NC(C)=C(Cl)C(NCC=2C=CC(O)=CC=2)=N1 LNOXGJSWKWKZBB-UHFFFAOYSA-N 0.000 description 2
- JISFNCDZECPCQP-UHFFFAOYSA-N 5-[[(5-chloro-2,6-dimethylpyrimidin-4-yl)amino]methyl]-2-(3-nitroimidazo[1,2-b]pyridazin-6-yl)oxyphenol Chemical compound CC1=NC(C)=C(Cl)C(NCC=2C=C(O)C(OC3=NN4C([N+]([O-])=O)=CN=C4C=C3)=CC=2)=N1 JISFNCDZECPCQP-UHFFFAOYSA-N 0.000 description 2
- CLKPMXSBUIYTAE-UHFFFAOYSA-N 5-chloro-2,6-dimethyl-n-[(4-phenylmethoxyphenyl)methyl]pyrimidin-4-amine;hydrochloride Chemical compound Cl.CC1=NC(C)=C(Cl)C(NCC=2C=CC(OCC=3C=CC=CC=3)=CC=2)=N1 CLKPMXSBUIYTAE-UHFFFAOYSA-N 0.000 description 2
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- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229960001180 norfloxacin Drugs 0.000 description 1
- OGJPXUAPXNRGGI-UHFFFAOYSA-N norfloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 OGJPXUAPXNRGGI-UHFFFAOYSA-N 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
- 229960001699 ofloxacin Drugs 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229960000381 omeprazole Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
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- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 229960005019 pantoprazole Drugs 0.000 description 1
- 229960001914 paromomycin Drugs 0.000 description 1
- UOZODPSAJZTQNH-LSWIJEOBSA-N paromomycin Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO UOZODPSAJZTQNH-LSWIJEOBSA-N 0.000 description 1
- 229960004236 pefloxacin Drugs 0.000 description 1
- FHFYDNQZQSQIAI-UHFFFAOYSA-N pefloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCN(C)CC1 FHFYDNQZQSQIAI-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229940056360 penicillin g Drugs 0.000 description 1
- SPPNVMTVMQOKSC-UHFFFAOYSA-A pentaaluminum decamagnesium hentriacontahydroxide disulfate hydrate Chemical compound O.[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg++].[Mg++].[Mg++].[Mg++].[Mg++].[Mg++].[Mg++].[Mg++].[Mg++].[Mg++].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O SPPNVMTVMQOKSC-UHFFFAOYSA-A 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
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- 150000002989 phenols Chemical class 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000002331 protein detection Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical class SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
- 229960004157 rabeprazole Drugs 0.000 description 1
- YREYEVIYCVEVJK-UHFFFAOYSA-N rabeprazole Chemical compound COCCCOC1=CC=NC(CS(=O)C=2NC3=CC=CC=C3N=2)=C1C YREYEVIYCVEVJK-UHFFFAOYSA-N 0.000 description 1
- VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 description 1
- 229960000620 ranitidine Drugs 0.000 description 1
- 229950004535 rebamipide Drugs 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229960001225 rifampicin Drugs 0.000 description 1
- 229960003040 rifaximin Drugs 0.000 description 1
- NZCRJKRKKOLAOJ-XRCRFVBUSA-N rifaximin Chemical compound OC1=C(C(O)=C2C)C3=C4N=C5C=C(C)C=CN5C4=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O NZCRJKRKKOLAOJ-XRCRFVBUSA-N 0.000 description 1
- IKQNRQOUOZJHTR-UWBRJAPDSA-N ritipenem Chemical compound S1C(COC(N)=O)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 IKQNRQOUOZJHTR-UWBRJAPDSA-N 0.000 description 1
- 229950004286 ritipenem Drugs 0.000 description 1
- 229960003320 roxatidine Drugs 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229950010458 sanfetrinem Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229960003177 sitafloxacin Drugs 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 229960005053 tinidazole Drugs 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- KHAUBYTYGDOYRU-IRXASZMISA-N trospectomycin Chemical compound CN[C@H]([C@H]1O2)[C@@H](O)[C@@H](NC)[C@H](O)[C@H]1O[C@H]1[C@]2(O)C(=O)C[C@@H](CCCC)O1 KHAUBYTYGDOYRU-IRXASZMISA-N 0.000 description 1
- 229950000976 trospectomycin Drugs 0.000 description 1
- 229960000497 trovafloxacin Drugs 0.000 description 1
- WVPSKSLAZQPAKQ-CDMJZVDBSA-N trovafloxacin Chemical compound C([C@H]1[C@@H]([C@H]1C1)N)N1C(C(=CC=1C(=O)C(C(O)=O)=C2)F)=NC=1N2C1=CC=C(F)C=C1F WVPSKSLAZQPAKQ-CDMJZVDBSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
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- Animal Behavior & Ethology (AREA)
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- Nitrogen Condensed Heterocyclic Rings (AREA)
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Abstract
A találmány szerinti (I) általános képletű benzilamino-pirimidin-vegyületek Helicobacter baktériumok ellen alkalmazhatók. A képletbenRl jelentése hidrogénatom, alkilcsoport vagy halogénatom; R2 jelentésehidrogénatom, alkilcsoport vagy halogénatom; R3 jelentésehidrogénatom, alkilcsoport vagy halogénatom; R4 jelentése hidrogénatomvagy alkilcsoport; R5 jelentése hidrogénatom, hidroxil-, alkil-,alkoxi-, fluorral teljesen vagy túlnyomórészt helyettesített alkoxi-,trifluor-metil-csoport vagy halogénatom; R6 jelentése hidrogénatom,hidroxil-, alkil-, alkoxi-, fluorral teljesen vagy túlnyomórészthelyettesített alkoxicsoport vagy halogénatom; R7 jelentésenitrocsoporttal és R9 és R10 csoporttal helyettesített ciklikus- vagybiciklikus-csoport, éspedig imidazol, imidazopirdazin vagyimidazopiridin; A jelentése alkiléncsoport; B jelentése kötés vagyalkiléncsoport; X jelentése O (oxigénatom); N-alkil-, NH vagy S(O)n;és Y jelentése CH vagy CR8; ahol R8 jelentése hidroxil-, alkil-,alkoxi-,fluorral teljesen vagy túlnyomórészt helyettesített alkoxi-,trifluor-metil-csoport vagy halogénatom; R9 jelentése hidrogénatom,alkilcsoport, halogénatom, nitro-, hidroxi-alkil- vagyalkilkarboniloxi-alkil-csoport; R10 jelentése hidrogénatom,alkilcsoport vagy nitrocsoport; és n értéke 0, 1 vagy 2. A találmánykiterjed a vegyületeket tartalmazó készítményekre is. Ó
Claims (20)
- * 4 ··♦···Η· :·:· <·Szabadalmi igénypontok1. (I) általános képletű vegyületek és sóik[mely képletbenRÍ jelentése hidrogénatom, 1-4 szénatomos alkil-csoport vagy halogénatom;R2 jelentése hidrogénatom, 1-4 szénatomos alkil-csoport vagy halogénatom;R3 jelentése hidrogénatom, 1-4 szénatomos alkil-csoport vagy halogénatom;R4 jelentése hidrogénatom vagy 1-4 szénatomos alkil-csoport;R5 jelentése hidrogénatom, hidroxil-, 1-4 szénatomos alkil-, 1-4 szénatomos alkoxi-, fluorral teljesen vagy túlnyomórészt helyettesített 1-4 szénatomos alkoxi-, trifluor-metil-csoport vagy halogénatom;R6 jelentése hidrogénatom, hidroxil-, 1-4 szénatomos alkil-, 1-4 szénatomos alkoxi-, fluorral teljesen vagy túlnyomórészt helyettesített 1-4 szénatomos alkoxi-csoport vagy halogénatom;R7 jelentése nitro-csoporttal és R9 és RIO csoporttal helyettesített ciklikus- vagy biciklikus-csoport, éspedig imidazol, imidazopiridazin vagy imidazopiridin;A jelentése 1-7 szénatomos alkilén-csoport;B jelentése kötés vagy 1-7 szénatomos alkilén-csoport;X jelentése O (oxigénatom), N-(l-4 szénatomos alkil)-, NH vagy S(O)n; ésY jelentése CH vagy CR8;aholR8 jelentése hidroxil-, 1-4 szénatomos alkil-, 1-4 szénatomos alkoxi-, fluorral teljesen vagy túlnyomórészt helyettesített 1-4 szénatomos alkoxi-, trifluor-metil-csoport vagy halogénatom;R9 jelentése hidrogénatom, 1-4 szénatomos alkil-csoport, halogénatom, nitro-, hidroxi-(l-4 szénatomos alkil)- vagy 1-4 szénatomos alkilkarboniloxi-(l-4 szénatomos alkil)-csoport;RIO jelentése hidrogénatom, 1-4 szénatomos alkil-csoport vagy nitro-csoport; és n értéke 0, 1 vagy 2].
- 2. Azl. igénypont szerinti vegyületek, amelyekben X S(0)n csoporttól eltérő jelentésű, ha egyidejűleg B jelentése kötés és A jelentése 1-6-szénatomos alkilén-csoport és az -A-NR4-(Rl)(R2)(R3)-pirimidin-4-il- és -X-B-R7-csoport egymáshoz viszonyítva 3-helyzetben (meta-helyzet) helyezkedik el.
- 3. Az 1. igénypont szerinti vegyületek, amelyekben X jelentése O (oxigénatom).
- 4. Azl. igénypont szerinti (I) általános képletű vegyületek és sóik, amelyekbenRÍ jelentése hidrogénatom, 1-4 szénatomos alkil-csoport vagy halogénatom;R2 jelentése hidrogénatom, 1-4 szénatomos alkil-csoport vagy halogénatom;R3 jelentése hidrogén- vagy halogénatom;R4 jelentése hidrogénatom vagy 1-4 szénatomos alkil-csoport;R5 jelentése hidrogénatom, hidroxil-, 1-4 szénatomos alkil-, 1-4 szénatomos alkoxi-, fluorral teljesen vagy túlnyomórészt helyettesített 1-4 szénatomos alkoxi-, trifluor-metil-csoport vagy halogénatom;R6 jelentése hidrogénatom, 1-4 szénatomos alkil-, 1-4 szénatomos alkoxi-csoport vagy halogénatom;R7 jelentése nitro-csoporttal és R9 és RIO csoporttal helyettesített ciklikus- vagy biciklikus-csoport, éspedig imidazol vagy imidazopiridazin;A jelentése metilén-csoport;B jelentése kötés vagy 1-4 szénatomos alkilén-csoport;X jelentése O (oxigénatom), NH vagy S(O)n; ésY jelentése CH vagy CR8;aholR8 jelentése hidrogénatom, hidroxil-, 1-4 szénatomos alkil-, 1-4 szénatomos alkoxi-, fluorral teljesen vagy túlnyomórészt helyettesített 1-4 szénatomos alkoxi-, trifluor-metil-csoport vagy halogénatom;R9 jelentése hidrogénatom;RIO jelentése hidrogénatom;n értéke 0.: ’ .
- 5. A 4. igénypont szerinti vegyületek, amelyekben X S(O)n csoporttól eltérő jelentésű, ha egyidejűleg B jelentése kötés és az -A-NR4-(Rl)(R2)(R3)-pirimidin-4-il- és -X-B-R7-csoport egymáshoz viszonyítva 3-helyzetben (meta-helyzet) helyezkedik el.
- 6. A 4. igénypont szerinti vegyületek, amelyekben X jelentése O (oxigénatom).
- 7. Az 1. igénypont szerinti (I) általános képletü vegyületek és sóik, amelyekbenRÍ jelentése hidrogénatom vagy metil-csoport;R2 jelentése hidrogénatom vagy metil-csoport;R3 jelentése hidrogén- vagy klóratom;R4 jelentése hidrogénatom vagy metil-csoport;R5 jelentése hidrogénatom, 1-4 szénatomos alkil-, 1-4 szénatomos alkoxi-, fluorral teljesen vagy túlnyomórészt helyettesített 1-4 szénatomos alkoxi-, trifluor-metil-csoport vagy halogénatom;R6 jelentése hidrogénatom, 1-4 szénatomos alkil-, 1-4 szénatomos alkoxi-csoport vagy halogénatom;R7 jelentése 3-nitro-imidazo[l,2-b]piridazin-6-il- vagy 2-metil-5-nitro-imidazol-l-il-csoport;A jelentése metilén-csoport;B jelentése kötés vagy 1-2 szénatomos alkilén-csoport;X jelentése O (oxigénatom), NH vagy S; ésY jelentése CH.
- 8. A 7. igénypont szerinti vegyületek, amelyekben X S atomtól eltérő jelentésű, ha egyidejűleg B jelentése kötés és az -A-NR4-(Rl)(R2)(R3)-pirimidin-4-il- és -X-B-R7csoport egymáshoz viszonyítva 3-helyzetben (meta-helyzet) helyezkedik el.
- 9. A 7. igénypont szerinti vegyületek, amelyekben X jelentése O (oxigénatom).
- 10. Az 1., 2., 3., 4., 5., 6., 7., 8. vagy 9. igénypont szerinti (I) általános képletü vegyületek, amelyekben B jelentése kötés és R7 jelentése 3-nitro-imidazo[l,2-b]piridazin-6-il-csoport.
- 11. Az 1. igénypont szerinti (I*) általános képletü vegyületek és sóik [mely képletbenRÍ jelentése hidrogénatom vagy metil-csoport;R2 jelentése hidrogénatom vagy metil-csoport;R3 jelentése hidrogén- vagy klóratom;R4 jelentése hidrogénatom vagy metil-csoport;R5 jelentése hidrogénatom, hidroxil-, metil-, metoxi-, etoxi-, ciklopropil-metoxi-, izobutoxi-, trifluor-metoxi-, difluor-metoxi-, trifluor-metil-csoport vagy klóratom;R6 jelentése hidrogénatom, metil-, metoxi-csoport vagy klóratom;R7 jelentése 3-nitro-imidazo[l,2-b]piridazin-6-il-csoport;A jelentése metilén-csoport;B jelentése kötés;X jelentése 0 (oxigénatom), NH vagy S; ésY jelentése CH.
- 12. All. igénypont szerinti (I*) általános képletü vegyületek és sóik, amelyekben RÍ jelentése hidrogénatom vagy 1-4 szénatomos alkil-csoport;R2 jelentése hidrogénatom vagy 1-4 szénatomos alkil-csoport;R3 jelentése hidrogén- vagy klóratom;R4 jelentése hidrogénatom;R5 jelentése hidrogénatom, hidroxil-, 1-4 szénatomos alkil-, 1-4 szénatomos alkoxi-, fluorral teljesen vagy túlnyomórészt helyettesített 1-4 szénatomos alkoxi-csoport vagy halogénatom;R6 jelentése hidrogénatom vagy 1-4 szénatomos alkoxi-csoport;R7 jelentése 3-nitro-imidazo[l,2-b]piridazin-6-il-csoport;A jelentése metilén-csoport;B jelentése kötés;X jelentése 0 (oxigénatom); ésY jelentése CH.
- 13. Azl. igénypont szerinti (I**) általános képletű vegyületek és sóik, amelyekbenRÍ jelentése hidrogénatom, 1-4 szénatomos alkil-csoport vagy halogénatom;R2 jelentése hidrogénatom, 1-4 szénatomos alkil-csoport vagy halogénatom;R3 jelentése hidrogén- vagy halogénatom;R4 jelentése hidrogénatom vagy 1-4 szénatomos alkil-csoport;R5 jelentése hidrogénatom, hidroxil-, 1-4 szénatomos alkil-, 1-4 szénatomos alkoxi-, fluorral teljesen vagy túlnyomórészt helyettesített 1-4 szénatomos alkoxi-, trifluor-metil-csoport vagy halogénatom;R6 jelentése hidrogénatom, 1-4 szénatomos alkil-, 1-4 szénatomos alkoxi-csoport vagy halogénatom;A jelentése metilén-csoport;Y jelentése CH vagy CR8;aholR8 jelentése hidrogénatom, hidroxil-, 1-4 szénatomos alkil-, 1-4 szénatomos alkoxi-, fluorral teljesen vagy túlnyomórészt helyettesített 1-4 szénatomos alkoxi-, trifluor-metil-csoport vagy halogénatom.
- 14. Az 1. igénypont szerinti (I**) általános képletű vegyületek és sóik, amelyekbenRÍ jelentése hidrogénatom vagy metil-csoport;R2 jelentése hidrogénatom vagy metil-csoport;R3 jelentése hidrogén- vagy klóratom;R4 jelentése hidrogénatom;R5 jelentése hidrogénatom, hidroxil-, 1-4 szénatomos alkil-, 1-4 szénatomos alkoxi-, fluorral teljesen vagy túlnyomórészt helyettesített 1-4 szénatomos alkoxi-csoport vagy halogénatom;R6 jelentése hidrogénatom vagy 1-4 szénatomos alkoxi-csoport;A jelentése metilén-csoport; ésY jelentése CH.
- 15. Azl. igénypont szerinti (I**) általános képletű vegyületek és sóik, amelyekbenRÍ jelentése metil-csoport;R2 jelentése metil-csoport;R3 jelentése klóratom;R4 jelentése hidrogénatom;R5 jelentése hidrogénatom, hidroxil-, 1-4 szénatomos alkil-, 1-4 szénatomos alkoxi-, fluorral teljesen vagy túlnyomórészt helyettesített 1-4 szénatomos alkoxi-csoport vagy halogénatom;R6 jelentése hidrogénatom vagy 1-4 szénatomos alkoxi-csoport;A jelentése metilén-csoport; ésY jelentése CH.
- 16. Az 1. igénypont szerinti (I**) általános képletű vegyületek és sóik, amelyekbenRÍ jelentése metil-csoport;R2 jelentése metil-csoport;R3 jelentése klóratom;R4 jelentése hidrogénatom;R5 jelentése hidrogénatom, hidroxil-, metil-, metoxi-, ciklopropil-metoxi-, 2,2,2-trifluor-etoxi-, difluor-metoxi-csoport, fluor-, klór- vagy brómatom;R6 jelentése hidrogénatom vagy metoxi-csoport;A jelentése metilén-csoport; ésY jelentése CH.
- 17. Az 1. igénypont szerinti (5-klór-2,6-dimetil-pirimidin-4-il)-[4-(3-nitro-imidazo-[1,2-b]piridazin-6-il-oxi)-benzil]-amin és sói.
- 18. Gyógyszer, amely valamely, az 1. igénypont szerinti (I) általános képletű vegyületet és/vagy gyógyászatilag alkalmas sóját és szokásos segédanyagokat tartalmaz.
- 19. Az 1. igénypont szerinti (I) általános képletű vegyületek és/vagy gyógyászatilag alkalmas sóik felhasználása Helicobacter baktériumok ellen.
- 20. Az 1. igénypont szerinti (I) általános képletű vegyületek és gyógyászatilag alkalmas sóik felhasználása Helicobacter baktériumok ellen felhasználható gyógyszerek előállítására.A bejelentő helyett a meghatalmazott:
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01112226 | 2001-05-18 | ||
| DE10139825 | 2001-08-14 | ||
| DE10162319 | 2001-12-19 | ||
| PCT/EP2002/005266 WO2002094832A1 (en) | 2001-05-18 | 2002-05-14 | New benzylaminopyrimidines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUP0400733A2 true HUP0400733A2 (hu) | 2004-07-28 |
| HUP0400733A3 HUP0400733A3 (en) | 2004-10-28 |
Family
ID=27214558
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0400733A HUP0400733A3 (en) | 2001-05-18 | 2002-05-14 | New benzylaminopyrimidines, their use and pharmaceutical compositions containing them |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6818642B2 (hu) |
| EP (1) | EP1395594A1 (hu) |
| JP (1) | JP2004529970A (hu) |
| AR (1) | AR035966A1 (hu) |
| CA (1) | CA2447676A1 (hu) |
| CZ (1) | CZ20033473A3 (hu) |
| EE (1) | EE200300563A (hu) |
| HU (1) | HUP0400733A3 (hu) |
| PL (1) | PL364090A1 (hu) |
| SK (1) | SK15572003A3 (hu) |
| WO (1) | WO2002094832A1 (hu) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1654251A4 (en) * | 2003-08-14 | 2009-03-11 | Smithkline Beecham Corp | CHEMICAL COMPOUNDS |
| US7939613B2 (en) * | 2005-04-22 | 2011-05-10 | The Hong Kong University Of Science And Technology | Fluorescent water-soluble conjugated polyene compounds that exhibit aggregation induced emission and methods of making and using same |
| CN103772369B (zh) | 2012-10-25 | 2016-12-21 | 沈阳中化农药化工研发有限公司 | 胡椒乙胺类化合物及其用途 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0717971A (ja) | 1993-07-02 | 1995-01-20 | Takeda Chem Ind Ltd | イミダゾール誘導体、その製造法及び用途 |
| WO1996016656A1 (en) | 1994-12-02 | 1996-06-06 | Takeda Chemical Industries, Ltd. | Condensed imidazole derivatives, their preparation and use |
| AU733552B2 (en) | 1996-12-20 | 2001-05-17 | Altana Pharma Ag | Imidazopyridazines |
| IL139530A0 (en) | 1998-05-23 | 2001-11-25 | Byk Gulden Lomberg Chem Fab | Pyrimidin-aminomethyl-pyridine derivatives, methods for preparation thereof and pharmaceutical compositions containing the same |
| SE9904044D0 (sv) | 1999-11-09 | 1999-11-09 | Astra Ab | Compounds |
| SE9904045D0 (sv) * | 1999-11-09 | 1999-11-09 | Astra Ab | Compounds |
-
2002
- 2002-05-13 AR ARP020101712A patent/AR035966A1/es not_active Application Discontinuation
- 2002-05-14 EE EEP200300563A patent/EE200300563A/xx unknown
- 2002-05-14 JP JP2002591505A patent/JP2004529970A/ja active Pending
- 2002-05-14 US US10/477,622 patent/US6818642B2/en not_active Expired - Fee Related
- 2002-05-14 CZ CZ20033473A patent/CZ20033473A3/cs unknown
- 2002-05-14 CA CA002447676A patent/CA2447676A1/en not_active Abandoned
- 2002-05-14 EP EP02743006A patent/EP1395594A1/en not_active Withdrawn
- 2002-05-14 HU HU0400733A patent/HUP0400733A3/hu unknown
- 2002-05-14 SK SK1557-2003A patent/SK15572003A3/sk unknown
- 2002-05-14 PL PL02364090A patent/PL364090A1/xx not_active Application Discontinuation
- 2002-05-14 WO PCT/EP2002/005266 patent/WO2002094832A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| PL364090A1 (en) | 2004-12-13 |
| EE200300563A (et) | 2004-02-16 |
| US6818642B2 (en) | 2004-11-16 |
| EP1395594A1 (en) | 2004-03-10 |
| JP2004529970A (ja) | 2004-09-30 |
| SK15572003A3 (sk) | 2004-06-08 |
| WO2002094832A1 (en) | 2002-11-28 |
| CA2447676A1 (en) | 2002-11-28 |
| HUP0400733A3 (en) | 2004-10-28 |
| CZ20033473A3 (en) | 2004-05-12 |
| US20040152714A1 (en) | 2004-08-05 |
| AR035966A1 (es) | 2004-07-28 |
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