SK81299A3 - Imidazopyridazine compounds, pharmaceutical composition containing the same and their use - Google Patents

Imidazopyridazine compounds, pharmaceutical composition containing the same and their use Download PDF

Info

Publication number: SK81299A3
Authority: SK; Slovakia
Prior art keywords: methyl; alkyl; chloro; chlorine; imidazol
Prior art date: 1996-12-20

Application number

SK812-99A

Other languages

English (en)

Slovak (sk)

Inventor

Peter Zimmermann

Jorg Senn-Bilfinger

Bernhard Kohl

Guido Hanauer

Stefan Postius

Wolfgang Opferkuch

Gerhard Grundler

Original Assignee

Byk Gulden Lomberg Chem Fab

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1996-12-20

Filing date

1997-12-18

Publication date

2000-01-18

1997-12-18 Application filed by Byk Gulden Lomberg Chem Fab filed Critical Byk Gulden Lomberg Chem Fab

2000-01-18 Publication of SK81299A3 publication Critical patent/SK81299A3/sk

Links

150000005233 imidazopyridazines Chemical class 0.000 title claims description 13
239000008194 pharmaceutical composition Substances 0.000 title claims description 7
241000589989 Helicobacter Species 0.000 claims abstract description 9
-1 trifluoromethoxy, hydroxyl Chemical group 0.000 claims description 512
229910052717 sulfur Inorganic materials 0.000 claims description 49
229910052760 oxygen Inorganic materials 0.000 claims description 48
239000001257 hydrogen Substances 0.000 claims description 41
229910052739 hydrogen Inorganic materials 0.000 claims description 41
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 36
150000002431 hydrogen Chemical class 0.000 claims description 36
239000011593 sulfur Substances 0.000 claims description 36
150000003839 salts Chemical class 0.000 claims description 35
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 32
239000001301 oxygen Substances 0.000 claims description 32
150000001204 N-oxides Chemical class 0.000 claims description 24
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 24
229910052736 halogen Inorganic materials 0.000 claims description 23
150000002367 halogens Chemical class 0.000 claims description 23
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 19
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
125000004076 pyridyl group Chemical group 0.000 claims description 16
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 11
125000002619 bicyclic group Chemical group 0.000 claims description 10
125000004122 cyclic group Chemical group 0.000 claims description 10
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 9
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 8
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 8
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 8
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 8
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 8
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 8
150000003536 tetrazoles Chemical class 0.000 claims description 8
125000000335 thiazolyl group Chemical group 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
WFIHKLWVLPBMIQ-UHFFFAOYSA-N [1,3]thiazolo[5,4-b]pyridine Chemical compound C1=CN=C2SC=NC2=C1 WFIHKLWVLPBMIQ-UHFFFAOYSA-N 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
NMJQBLVCTWZTJG-UHFFFAOYSA-M 1,2-dimethyl-1-[3-(2-methylphenoxy)-3-phenylpropyl]piperidin-1-ium;bromide Chemical group [Br-].CC1CCCC[N+]1(C)CCC(C=1C=CC=CC=1)OC1=CC=CC=C1C NMJQBLVCTWZTJG-UHFFFAOYSA-M 0.000 claims description 4
GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 4
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 4
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 4
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 4
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 4
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 4
239000000546 pharmaceutical excipient Substances 0.000 claims description 4
ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 4
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 4
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 4
XWMXMWHHTIEXRE-UHFFFAOYSA-N thiadiazole 1-oxide Chemical compound O=S1C=CN=N1 XWMXMWHHTIEXRE-UHFFFAOYSA-N 0.000 claims description 4
CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 claims description 4
229930192474 thiophene Natural products 0.000 claims description 4
150000003852 triazoles Chemical class 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 2
POHFGEGSJPLGNI-UHFFFAOYSA-N 1-oxidopyridin-1-ium;pyridine Chemical compound C1=CC=NC=C1.[O-][N+]1=CC=CC=C1 POHFGEGSJPLGNI-UHFFFAOYSA-N 0.000 claims description 2
125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
WQZGKKKJIJFFOK-UHFFFAOYSA-N hexopyranose Chemical compound OCC1OC(O)C(O)C(O)C1O WQZGKKKJIJFFOK-UHFFFAOYSA-N 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 112
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 78
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
239000000243 solution Substances 0.000 description 54
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 32
125000001424 substituent group Chemical group 0.000 description 31
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
239000000203 mixture Substances 0.000 description 28
239000000725 suspension Substances 0.000 description 28
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 25
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 25
239000007787 solid Substances 0.000 description 25
239000002244 precipitate Substances 0.000 description 24
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 24
239000005977 Ethylene Substances 0.000 description 23
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 22
238000001816 cooling Methods 0.000 description 19
239000000284 extract Substances 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
229910052943 magnesium sulfate Inorganic materials 0.000 description 16
235000019341 magnesium sulphate Nutrition 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
PBRVBSFCOONPOY-UHFFFAOYSA-N 6-[3-[2-(chloromethyl)-3-methylpyridin-4-yl]sulfanylpropylsulfanyl]-3-nitroimidazo[1,2-b]pyridazine Chemical compound C1=CN=C(CCl)C(C)=C1SCCCSC1=NN2C([N+]([O-])=O)=CN=C2C=C1 PBRVBSFCOONPOY-UHFFFAOYSA-N 0.000 description 14
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
238000010992 reflux Methods 0.000 description 14
YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 13
UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical compound ClC1=NC=CC=N1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 description 13
239000000460 chlorine Substances 0.000 description 13
229910052801 chlorine Inorganic materials 0.000 description 13
AYPSHJCKSDNETA-UHFFFAOYSA-N 2-chloro-1h-benzimidazole Chemical compound C1=CC=C2NC(Cl)=NC2=C1 AYPSHJCKSDNETA-UHFFFAOYSA-N 0.000 description 12
WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
IOHQJEIBMAYHTF-UHFFFAOYSA-N [Cl].ClC Chemical compound [Cl].ClC IOHQJEIBMAYHTF-UHFFFAOYSA-N 0.000 description 11
238000000034 method Methods 0.000 description 11
XTIGGAHUZJWQMD-UHFFFAOYSA-N 1-chloro-2-methoxyethane Chemical compound COCCCl XTIGGAHUZJWQMD-UHFFFAOYSA-N 0.000 description 10
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 10
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
238000000746 purification Methods 0.000 description 10
150000003254 radicals Chemical class 0.000 description 10
ZFHHWMWWIKSYTK-UHFFFAOYSA-N 2-chloro-6-methylsulfanyl-1h-benzimidazole Chemical compound CSC1=CC=C2N=C(Cl)NC2=C1 ZFHHWMWWIKSYTK-UHFFFAOYSA-N 0.000 description 9
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
239000012299 nitrogen atmosphere Substances 0.000 description 9
NFJCHWSGZQITHG-UHFFFAOYSA-N 2-(2-chloroimidazol-1-yl)-3-methylpyridine Chemical compound CC1=CC=CN=C1N1C(Cl)=NC=C1 NFJCHWSGZQITHG-UHFFFAOYSA-N 0.000 description 8
FQWRFDNWGQGROK-UHFFFAOYSA-N 2-(2-chloroimidazol-1-yl)pyridine Chemical compound ClC1=NC=CN1C1=CC=CC=N1 FQWRFDNWGQGROK-UHFFFAOYSA-N 0.000 description 8
SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 8
QEYMMOKECZBKAC-UHFFFAOYSA-N 3-chloropropanoic acid Chemical compound OC(=O)CCCl QEYMMOKECZBKAC-UHFFFAOYSA-N 0.000 description 8
DHELIGKVOGTMGF-UHFFFAOYSA-N 5-chloro-1-phenyltetrazole Chemical compound ClC1=NN=NN1C1=CC=CC=C1 DHELIGKVOGTMGF-UHFFFAOYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
239000012043 crude product Substances 0.000 description 8
239000000126 substance Substances 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
QJKIZIZPTXGHGI-UHFFFAOYSA-N 2-chloro-6-methylsulfonyl-1h-benzimidazole Chemical compound CS(=O)(=O)C1=CC=C2N=C(Cl)NC2=C1 QJKIZIZPTXGHGI-UHFFFAOYSA-N 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 7
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 7
229910021529 ammonia Inorganic materials 0.000 description 7
238000001914 filtration Methods 0.000 description 7
238000003756 stirring Methods 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
JIQXRLOYKOJECL-UHFFFAOYSA-N 1-(2-chloroethoxy)-2-methoxyethane Chemical compound COCCOCCCl JIQXRLOYKOJECL-UHFFFAOYSA-N 0.000 description 6
FNAKEMBTTABVAN-UHFFFAOYSA-N 2-(2-chloro-3h-benzimidazol-5-yl)-1,3-thiazole Chemical compound C1=C2NC(Cl)=NC2=CC=C1C1=NC=CS1 FNAKEMBTTABVAN-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
239000003921 oil Substances 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 description 5
VHCQZLWGOFKVGZ-UHFFFAOYSA-N 4-(5-chlorotetrazol-1-yl)phenol Chemical compound C1=CC(O)=CC=C1N1C(Cl)=NN=N1 VHCQZLWGOFKVGZ-UHFFFAOYSA-N 0.000 description 5
PVMNPAUTCMBOMO-UHFFFAOYSA-N 4-chloropyridine Chemical compound ClC1=CC=NC=C1 PVMNPAUTCMBOMO-UHFFFAOYSA-N 0.000 description 5
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
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 5
229960000583 acetic acid Drugs 0.000 description 5
BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 5
238000001035 drying Methods 0.000 description 5
239000003480 eluent Substances 0.000 description 5
239000005457 ice water Substances 0.000 description 5
238000010898 silica gel chromatography Methods 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 4
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 4
241000590002 Helicobacter pylori Species 0.000 description 4
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 description 4
239000013543 active substance Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
125000001309 chloro group Chemical group Cl* 0.000 description 4
201000010099 disease Diseases 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
229940037467 helicobacter pylori Drugs 0.000 description 4
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
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239000012312 sodium hydride Substances 0.000 description 4
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125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
229960000282 metronidazole Drugs 0.000 description 1
VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
HSKNJSHFPPHTAQ-UHFFFAOYSA-N n-(2-chloroethyl)acetamide Chemical compound CC(=O)NCCCl HSKNJSHFPPHTAQ-UHFFFAOYSA-N 0.000 description 1
VEZDAWXAFNOXDO-UHFFFAOYSA-N n-[[2-(1h-benzimidazol-2-ylsulfanylmethyl)-3-chloropyridin-4-yl]methyl]-2-(3-nitroimidazo[1,2-b]pyridazin-6-yl)sulfanylethanamine Chemical compound C1=CC=C2NC(SCC=3N=CC=C(C=3Cl)CNCCSC=3C=CC4=NC=C(N4N=3)[N+](=O)[O-])=NC2=C1 VEZDAWXAFNOXDO-UHFFFAOYSA-N 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical compound NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 description 1
229960000564 nitrofurantoin Drugs 0.000 description 1
NXFQHRVNIOXGAQ-YCRREMRBSA-N nitrofurantoin Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)NC(=O)C1 NXFQHRVNIOXGAQ-YCRREMRBSA-N 0.000 description 1
229960001907 nitrofurazone Drugs 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[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
SBQLYHNEIUGQKH-UHFFFAOYSA-N omeprazole Chemical compound N1=C2[CH]C(OC)=CC=C2N=C1S(=O)CC1=NC=C(C)C(OC)=C1C SBQLYHNEIUGQKH-UHFFFAOYSA-N 0.000 description 1
229960000381 omeprazole Drugs 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
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
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
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
239000011591 potassium Chemical class 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
RYVMUASDIZQXAA-UHFFFAOYSA-N pyranoside Natural products O1C2(OCC(C)C(OC3C(C(O)C(O)C(CO)O3)O)C2)C(C)C(C2(CCC3C4(C)CC5O)C)C1CC2C3CC=C4CC5OC(C(C1O)O)OC(CO)C1OC(C1OC2C(C(OC3C(C(O)C(O)C(CO)O3)O)C(O)C(CO)O2)O)OC(CO)C(O)C1OC1OCC(O)C(O)C1O RYVMUASDIZQXAA-UHFFFAOYSA-N 0.000 description 1
WFJZBOIOPMOUCB-UHFFFAOYSA-N pyridazine;hydrochloride Chemical compound Cl.C1=CC=NN=C1 WFJZBOIOPMOUCB-UHFFFAOYSA-N 0.000 description 1
125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 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
239000011541 reaction mixture Substances 0.000 description 1
XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
239000012047 saturated solution Substances 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
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229950004351 telenzepine Drugs 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229960005053 tinidazole Drugs 0.000 description 1
239000010936 titanium Chemical class 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
JQZIKLPHXXBMCA-UHFFFAOYSA-N triphenylmethanethiol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(S)C1=CC=CC=C1 JQZIKLPHXXBMCA-UHFFFAOYSA-N 0.000 description 1

Classifications

- 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
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Paper (AREA)
Cosmetics (AREA)
Luminescent Compositions (AREA)
Saccharide Compounds (AREA)

SK812-99A 1996-12-20 1997-12-18 Imidazopyridazine compounds, pharmaceutical composition containing the same and their use SK81299A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE19653375		1996-12-20
EP97101668		1997-02-04
PCT/EP1997/007133 WO1998028299A2 (en)	1996-12-20	1997-12-18	Imidazopyridazines

Publications (1)

Publication Number	Publication Date
SK81299A3 true SK81299A3 (en)	2000-01-18

Family

ID=26032538

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK812-99A SK81299A3 (en)	1996-12-20	1997-12-18	Imidazopyridazine compounds, pharmaceutical composition containing the same and their use

Country Status (19)

Country	Link
US (1)	US6043242A (et)
EP (1)	EP0946559A2 (et)
JP (1)	JP2001506666A (et)
KR (1)	KR20000057649A (et)
CN (1)	CN1105720C (et)
AU (1)	AU733552B2 (et)
BR (1)	BR9714049A (et)
CA (1)	CA2275601A1 (et)
EA (1)	EA001734B1 (et)
EE (1)	EE03690B1 (et)
HU (1)	HUP0000460A3 (et)
IL (1)	IL130348A (et)
NO (1)	NO312729B1 (et)
NZ (1)	NZ336034A (et)
PL (1)	PL334194A1 (et)
SK (1)	SK81299A3 (et)
TR (1)	TR199901386T2 (et)
UA (1)	UA57056C2 (et)
WO (1)	WO1998028299A2 (et)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2362930C (en) *	1999-02-26	2010-10-05	Nitromed, Inc.	Nitrosated and nitrosylated proton pump inhibitors, compositions and methods of use
US6455554B1 (en)	1999-06-07	2002-09-24	Targacept, Inc.	Oxopyridinyl pharmaceutical compositions and methods for use
US20030085387A1 (en) *	2000-05-31	2003-05-08	Takahiro Fujiyama	Optical materials and optical part each containing aromatic sulfide compound and aromatic sulfide compound
AR035966A1 (es)	2001-05-18	2004-07-28	Altana Pharma Ag	Un compuesto de bencilaminopirimidina, un medicamento que lo comprende y el uso del mismo
CA2581454A1 (en) *	2004-09-23	2006-03-30	Reddy Us Therapeutics, Inc.	Novel pyrimidine compounds, process for their preparation and compositions containing them
BRPI0619158A2 (pt)	2005-12-05	2011-09-20	Astrazeneca Ab	processo para preparar forma que não que não seja sal de esomeprazol, composto, formulação farmacêutica, e, método de tratamento
AR076601A1 (es)	2009-05-21	2011-06-22	Chlorion Pharma Inc	Pirimidinas como agentes terapeuticos
CN108129703A (zh) *	2017-11-13	2018-06-08	孝感市锐思新材科技有限公司	一种塑料抗菌材料的制备方法
CN108047216B (zh) *	2017-12-06	2020-11-10	石家庄学院	一种3,4-二苯基吡唑化合物及其制备和应用
CN111226956B (zh) *	2019-11-26	2021-10-26	贵州医科大学	3,6-二取代咪唑[1,2-b]哒嗪类衍生物在制备抑制植物病原真菌杀菌剂中的应用
JP2025541771A (ja)	2022-12-02	2025-12-23	ニューモラセラピューティクスインコーポレイテッド	神経障害を処置する方法
JPWO2024185814A1 (et) *	2023-03-06	2024-09-12

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4569932A (en) *	1982-11-12	1986-02-11	University Of Northern Iowa Foundations	Low toxicity radiation sensitizer
US4569934A (en) *	1984-10-09	1986-02-11	American Cyanamid Company	Imidazo[1,2-b]pyridazines
PH27291A (en) *	1989-01-31	1993-05-04	Takeda Chemical Industries Ltd	Imidazolpyrimidazines their production and use
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
JPH0820584A (ja) *	1994-07-04	1996-01-23	Takeda Chem Ind Ltd	イミダゾール誘導体及びその用途

1997
- 1997-12-18 JP JP52836098A patent/JP2001506666A/ja active Pending
- 1997-12-18 HU HU0000460A patent/HUP0000460A3/hu unknown
- 1997-12-18 UA UA99074154A patent/UA57056C2/uk unknown
- 1997-12-18 US US09/319,937 patent/US6043242A/en not_active Expired - Fee Related
- 1997-12-18 SK SK812-99A patent/SK81299A3/sk unknown
- 1997-12-18 EE EEP199900234A patent/EE03690B1/et not_active IP Right Cessation
- 1997-12-18 KR KR1019990705454A patent/KR20000057649A/ko not_active Ceased
- 1997-12-18 EP EP97954426A patent/EP0946559A2/en not_active Withdrawn
- 1997-12-18 CN CN97181815A patent/CN1105720C/zh not_active Expired - Fee Related
- 1997-12-18 TR TR1999/01386T patent/TR199901386T2/xx unknown
- 1997-12-18 NZ NZ336034A patent/NZ336034A/xx unknown
- 1997-12-18 AU AU58579/98A patent/AU733552B2/en not_active Ceased
- 1997-12-18 PL PL97334194A patent/PL334194A1/xx unknown
- 1997-12-18 IL IL13034897A patent/IL130348A/xx active IP Right Grant
- 1997-12-18 CA CA002275601A patent/CA2275601A1/en not_active Abandoned
- 1997-12-18 WO PCT/EP1997/007133 patent/WO1998028299A2/en not_active Ceased
- 1997-12-18 BR BR9714049-0A patent/BR9714049A/pt not_active IP Right Cessation
- 1997-12-18 EA EA199900534A patent/EA001734B1/ru not_active IP Right Cessation
1999
- 1999-06-21 NO NO19993050A patent/NO312729B1/no unknown

Also Published As

Publication number	Publication date
WO1998028299A3 (en)	1998-08-13
NO312729B1 (no)	2002-06-24
IL130348A (en)	2003-06-24
CA2275601A1 (en)	1998-07-02
NO993050L (no)	1999-06-21
TR199901386T2 (en)	1999-09-21
HUP0000460A2 (hu)	2001-02-28
WO1998028299A2 (en)	1998-07-02
KR20000057649A (ko)	2000-09-25
HUP0000460A3 (en)	2001-04-28
NO993050D0 (no)	1999-06-21
EE9900234A (et)	1999-12-15
JP2001506666A (ja)	2001-05-22
EP0946559A2 (en)	1999-10-06
IL130348A0 (en)	2000-06-01
CN1105720C (zh)	2003-04-16
EA001734B1 (ru)	2001-08-27
NZ336034A (en)	2000-09-29
UA57056C2 (uk)	2003-06-16
CN1246120A (zh)	2000-03-01
EE03690B1 (et)	2002-04-15
BR9714049A (pt)	2000-05-09
US6043242A (en)	2000-03-28
AU733552B2 (en)	2001-05-17
AU5857998A (en)	1998-07-17
EA199900534A1 (ru)	2000-02-28
PL334194A1 (en)	2000-02-14

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AU2008277628B2 (en)	2012-03-15	Bicyclic heteroaryl compounds and their use as kinase inhibitors
US5859030A (en)	1999-01-12	Substituted arylalkylthioalkylthiopyridines for use in the control of helicobacter bacteria
US6043242A (en)	2000-03-28	Imidazopyridazines
US6162809A (en)	2000-12-19	Pyridylthio compounds for controlling helicobacter bacteria
US6395732B1 (en)	2002-05-28	Pyrimidin-aminomethyl-pyridine derivatives, their preparation and their use in the control of helicobacter bacteria
US6107312A (en)	2000-08-22	Thiopyridines for use in the control of helicobacter bacteria
FI110778B (fi)	2003-03-31	Menetelmä terapeuttisesti käyttökelpoisten substituoitujen aryylitioalkyylitiopyridiinien valmistamiseksi
AU760769B2 (en)	2003-05-22	Quinoline-aminomethyl-pyridyl derivatives with anti-helicobacter activity
US5922720A (en)	1999-07-13	Piperazinothiopyridines for the control of Helicobacter bacteria
US20040158066A1 (en)	2004-08-12	Novel pyridylmethylaminopyrimidines
MXPA99005858A (en)	2000-01-01	Imidazopyridazines
CZ222499A3 (cs)	2000-04-12	Imidazopyridazinové deriváty
HK1036067B (en)	2005-05-13	Pyrimidin-aminomethyl-pyridine derivatives, their preparation and their use in the control of helicobacter bacteria
CZ20004376A3 (cs)	2001-07-11	Deriváty pyrimidin-aminomethyl-pyridinii
AU2002314064A1 (en)	2002-12-03	Novel pyridylmethylaminopyrimidines