NO312729B1 - Imidazopyridaziner - Google Patents

Imidazopyridaziner Download PDF

Info

Publication number: NO312729B1
Authority: NO; Norway
Prior art keywords: alkyl; sulfur; oxygen; mmol; hydrogen
Prior art date: 1996-12-20

Application number

NO19993050A

Other languages

English (en)

Norwegian (no)

Other versions

NO993050D0 (no

NO993050L (no

Inventor

Peter Zimmermann

Joerg 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

1999-06-21

Publication date

2002-06-24

1999-06-21 Application filed by Byk Gulden Lomberg Chem Fab filed Critical Byk Gulden Lomberg Chem Fab

1999-06-21 Publication of NO993050D0 publication Critical patent/NO993050D0/no

1999-06-21 Publication of NO993050L publication Critical patent/NO993050L/no

2002-06-24 Publication of NO312729B1 publication Critical patent/NO312729B1/no

Links

150000001875 compounds Chemical class 0.000 claims description 107
-1 hexopyranoses Chemical compound 0.000 claims description 70
150000003839 salts Chemical class 0.000 claims description 42
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 36
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 36
229910052760 oxygen Inorganic materials 0.000 claims description 36
239000001301 oxygen Substances 0.000 claims description 36
239000001257 hydrogen Substances 0.000 claims description 32
229910052739 hydrogen Inorganic materials 0.000 claims description 32
239000000203 mixture Substances 0.000 claims description 32
229910052717 sulfur Inorganic materials 0.000 claims description 32
239000011593 sulfur Substances 0.000 claims description 31
150000002431 hydrogen Chemical class 0.000 claims description 30
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
125000000217 alkyl group Chemical group 0.000 claims description 20
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 16
125000004076 pyridyl group Chemical group 0.000 claims description 16
125000000229 (C1-C4)alkoxy group Chemical group 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
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical class 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
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-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
241000589989 Helicobacter Species 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 6
239000000546 pharmaceutical excipient Substances 0.000 claims description 5
229940079593 drug Drugs 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 3
125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
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 Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 61
239000000243 solution Substances 0.000 description 57
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
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 34
239000007787 solid Substances 0.000 description 34
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
239000000725 suspension Substances 0.000 description 28
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
239000002244 precipitate Substances 0.000 description 23
238000001816 cooling Methods 0.000 description 18
239000000284 extract Substances 0.000 description 18
229910052943 magnesium sulfate Inorganic materials 0.000 description 17
235000019341 magnesium sulphate Nutrition 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
238000010992 reflux Methods 0.000 description 15
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
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
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 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
238000000034 method Methods 0.000 description 12
239000012299 nitrogen atmosphere Substances 0.000 description 12
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
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
238000000746 purification Methods 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
150000003254 radicals Chemical class 0.000 description 9
239000012043 crude product Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 7
229910021529 ammonia Inorganic materials 0.000 description 7
238000001914 filtration Methods 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000001035 drying Methods 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
239000003921 oil Substances 0.000 description 6
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
239000000126 substance Substances 0.000 description 6
NEKMBLKAKOUTAX-UHFFFAOYSA-N 3-nitro-5h-imidazo[1,2-b]pyridazine-6-thione Chemical compound C1=CC(=S)NN2C([N+](=O)[O-])=CN=C21 NEKMBLKAKOUTAX-UHFFFAOYSA-N 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
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 5
239000005864 Sulphur Substances 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
239000003480 eluent Substances 0.000 description 5
239000005457 ice water Substances 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
JYWKEVKEKOTYEX-UHFFFAOYSA-N 2,6-dibromo-4-chloroiminocyclohexa-2,5-dien-1-one Chemical compound ClN=C1C=C(Br)C(=O)C(Br)=C1 JYWKEVKEKOTYEX-UHFFFAOYSA-N 0.000 description 3
JWAWZBZHCLQOHR-UHFFFAOYSA-N 2-[[2-(1h-benzimidazol-2-ylsulfanylmethyl)-3-chloropyridin-4-yl]-methylamino]ethanol Chemical compound OCCN(C)C1=CC=NC(CSC=2NC3=CC=CC=C3N=2)=C1Cl JWAWZBZHCLQOHR-UHFFFAOYSA-N 0.000 description 3
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 3
241000590002 Helicobacter pylori Species 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
DPAKHEBMASRRTD-UHFFFAOYSA-N [4-(3-chloropropoxy)-3-methylpyridin-2-yl]methanol Chemical compound CC1=C(OCCCCl)C=CN=C1CO DPAKHEBMASRRTD-UHFFFAOYSA-N 0.000 description 3
239000012300 argon atmosphere Substances 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
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000001530 fumaric acid Substances 0.000 description 3
210000004211 gastric acid Anatomy 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
229940037467 helicobacter pylori Drugs 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000000047 product Substances 0.000 description 3
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
238000000926 separation method Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
239000003826 tablet Substances 0.000 description 3
UEAIOHHGRGSGGJ-UHFFFAOYSA-N (4-chloropyridin-2-yl)methanol Chemical compound OCC1=CC(Cl)=CC=N1 UEAIOHHGRGSGGJ-UHFFFAOYSA-N 0.000 description 2
PYEMQZVLGRZLJS-UHFFFAOYSA-N 2-[[2-(hydroxymethyl)pyridin-4-yl]-methylamino]ethanol Chemical compound OCCN(C)C1=CC=NC(CO)=C1 PYEMQZVLGRZLJS-UHFFFAOYSA-N 0.000 description 2
UPROJDCNZYVETO-UHFFFAOYSA-N 2-[[3-chloro-2-(chloromethyl)pyridin-4-yl]-methylamino]ethanol Chemical compound OCCN(C)C1=CC=NC(CCl)=C1Cl UPROJDCNZYVETO-UHFFFAOYSA-N 0.000 description 2
DCIOIMWRIGTQOP-UHFFFAOYSA-N 2-[[3-chloro-2-(hydroxymethyl)pyridin-4-yl]-methylamino]ethanol Chemical compound OCCN(C)C1=CC=NC(CO)=C1Cl DCIOIMWRIGTQOP-UHFFFAOYSA-N 0.000 description 2
IHEMNLDSTXKDPL-UHFFFAOYSA-N 3-[2-(hydroxymethyl)-3-methylpyridin-4-yl]oxypropan-1-ol Chemical compound CC1=C(CO)N=CC=C1OCCCO IHEMNLDSTXKDPL-UHFFFAOYSA-N 0.000 description 2
BEMOQOKAFQXXOM-UHFFFAOYSA-N 3-[[2-(1h-benzimidazol-2-ylsulfanylmethyl)-3-chloropyridin-4-yl]-methylamino]propan-1-ol Chemical compound OCCCN(C)C1=CC=NC(CSC=2NC3=CC=CC=C3N=2)=C1Cl BEMOQOKAFQXXOM-UHFFFAOYSA-N 0.000 description 2
VFTDARXSRHUGIM-UHFFFAOYSA-N 3-[[3-chloro-2-(chloromethyl)pyridin-4-yl]-methylamino]propan-1-ol Chemical compound OCCCN(C)C1=CC=NC(CCl)=C1Cl VFTDARXSRHUGIM-UHFFFAOYSA-N 0.000 description 2
KTSXIICOIKZGGR-UHFFFAOYSA-N 3-[[3-chloro-2-(hydroxymethyl)pyridin-4-yl]-methylamino]propan-1-ol Chemical compound OCCCN(C)C1=CC=NC(CO)=C1Cl KTSXIICOIKZGGR-UHFFFAOYSA-N 0.000 description 2
UTXVTZJWDRBHTP-UHFFFAOYSA-N 3-chloro-n-(2-chloroethyl)-2-(chloromethyl)-n-methylpyridin-4-amine Chemical compound ClCCN(C)C1=CC=NC(CCl)=C1Cl UTXVTZJWDRBHTP-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
239000005977 Ethylene Substances 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 2
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
DKNLQVYVOSJLFS-UHFFFAOYSA-N [3-chloro-4-[2-chloroethyl(methyl)amino]pyridin-2-yl]methanol Chemical compound ClCCN(C)C1=CC=NC(CO)=C1Cl DKNLQVYVOSJLFS-UHFFFAOYSA-N 0.000 description 2
OAVSWCUZHPOIAY-UHFFFAOYSA-N [3-chloro-4-[2-chloroethyl(methyl)amino]pyridin-2-yl]methyl acetate Chemical compound ClCCN(C)C1=CC=NC(COC(C)=O)=C1Cl OAVSWCUZHPOIAY-UHFFFAOYSA-N 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
235000011056 potassium acetate Nutrition 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
RTWMJHUHCFTRAG-WLHGVMLRSA-N (E)-but-2-enedioic acid 6-[3-[2-(2-methoxyethylsulfanylmethyl)-3-methylpyridin-4-yl]sulfanylpropylsulfanyl]-3-nitroimidazo[1,2-b]pyridazine Chemical compound OC(=O)\C=C\C(O)=O.COCCSCC1=NC=CC(SCCCSC2=NN3C([N+]([O-])=O)=CN=C3C=C2)=C1C RTWMJHUHCFTRAG-WLHGVMLRSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
MOXZSKYLLSPATM-UHFFFAOYSA-N 1-(4-hydroxyphenyl)-2h-tetrazole-5-thione Chemical compound C1=CC(O)=CC=C1N1C(=S)N=NN1 MOXZSKYLLSPATM-UHFFFAOYSA-N 0.000 description 1
GGZHVNZHFYCSEV-UHFFFAOYSA-N 1-Phenyl-5-mercaptotetrazole Chemical compound SC1=NN=NN1C1=CC=CC=C1 GGZHVNZHFYCSEV-UHFFFAOYSA-N 0.000 description 1
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239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
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
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
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
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
229960000564 nitrofurantoin Drugs 0.000 description 1
229960001907 nitrofurazone Drugs 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
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
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
230000002093 peripheral effect Effects 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
RMHMFHUVIITRHF-UHFFFAOYSA-N pirenzepine Chemical compound C1CN(C)CCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=CC=C21 RMHMFHUVIITRHF-UHFFFAOYSA-N 0.000 description 1
229960004633 pirenzepine Drugs 0.000 description 1
150000007519 polyprotic acids Polymers 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
239000000843 powder Substances 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
KFHJGCJNALDXEB-UHFFFAOYSA-N s-[[3-methyl-4-[3-(3-nitroimidazo[1,2-b]pyridazin-6-yl)sulfanylpropylsulfanyl]pyridin-2-yl]methyl] ethanethioate Chemical compound CC(=O)SCC1=NC=CC(SCCCSC2=NN3C([N+]([O-])=O)=CN=C3C=C2)=C1C KFHJGCJNALDXEB-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
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 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
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
229960005053 tinidazole Drugs 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)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Cosmetics (AREA)
Luminescent Compositions (AREA)
Paper (AREA)

NO19993050A 1996-12-20 1999-06-21 Imidazopyridaziner NO312729B1 (no)

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 (3)

Publication Number	Publication Date
NO993050D0 NO993050D0 (no)	1999-06-21
NO993050L NO993050L (no)	1999-06-21
NO312729B1 true NO312729B1 (no)	2002-06-24

Family

ID=26032538

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19993050A NO312729B1 (no)	1996-12-20	1999-06-21	Imidazopyridaziner

Country Status (19)

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

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* Cited by examiner, † Cited by third party
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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
KR20020044134A (ko) *	2000-05-31	2002-06-14	사토 아키오	방향족술피드화합물을 사용한 광학재료 및 광학부품 및방향족술피드화합물
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
WO2006034473A2 (en) *	2004-09-23	2006-03-30	Reddy Us Therapeutics, Inc.	Novel pyrimidine compounds, process for their preparation and compositions containing them
AU2006323245B2 (en)	2005-12-05	2011-03-03	Astrazeneca Ab	New process for the preparation of esomeprazole non-salt form
WO2010132999A1 (en)	2009-05-21	2010-11-25	Chlorion Pharma, Inc.	Methyl sulfanyl pyrmidmes useful as antiinflammatories, analgesics, and antiepileptics
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
WO2024119067A1 (en)	2022-12-02	2024-06-06	Neumora Therapeutics, Inc.	Methods of treating neurological disorders
WO2024185814A1 (ja) *	2023-03-06	2024-09-12	Ａｇｃ株式会社	トリチルスルファニル基含有アリール化合物の製造方法

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

Also Published As

Publication number	Publication date
KR20000057649A (ko)	2000-09-25
IL130348A (en)	2003-06-24
WO1998028299A3 (en)	1998-08-13
CA2275601A1 (en)	1998-07-02
EE9900234A (et)	1999-12-15
BR9714049A (pt)	2000-05-09
HUP0000460A2 (hu)	2001-02-28
UA57056C2 (ru)	2003-06-16
NO993050D0 (no)	1999-06-21
TR199901386T2 (en)	1999-09-21
AU733552B2 (en)	2001-05-17
JP2001506666A (ja)	2001-05-22
PL334194A1 (en)	2000-02-14
SK81299A3 (en)	2000-01-18
EP0946559A2 (en)	1999-10-06
NZ336034A (en)	2000-09-29
CN1246120A (zh)	2000-03-01
EA199900534A1 (ru)	2000-02-28
EA001734B1 (ru)	2001-08-27
EE03690B1 (et)	2002-04-15
HUP0000460A3 (en)	2001-04-28
CN1105720C (zh)	2003-04-16
IL130348A0 (en)	2000-06-01
AU5857998A (en)	1998-07-17
US6043242A (en)	2000-03-28
WO1998028299A2 (en)	1998-07-02
NO993050L (no)	1999-06-21

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AU2008277628B2 (en)	2012-03-15	Bicyclic heteroaryl compounds and their use as kinase inhibitors
EP2727910B1 (en)	2016-03-16	Pyridin-2-yl-thiourea and Pyridin-2-yl-amine derivatives as intermediates for the preparation of Pyridin-2yl-amino-1,2,4-thiadiazole glucokinase activators
CZ20012635A3 (cs)	2001-11-14	Aromatické heterocyklické sloučeniny, způsob jejich výroby a jejich pouľití
NO312729B1 (no)	2002-06-24	Imidazopyridaziner
US5859030A (en)	1999-01-12	Substituted arylalkylthioalkylthiopyridines for use in the control of helicobacter bacteria
AU702609B2 (en)	1999-02-25	Pyridylthio compounds for controlling helicobacter bacteria
DE69922655T2 (de)	2006-03-02	Pyrimidin-Aminomethyl-Pyridin Derivate; deren Herstellung und deren Verwendung gegen Helicobacter Bakterien
AU760769B2 (en)	2003-05-22	Quinoline-aminomethyl-pyridyl derivatives with anti-helicobacter activity
US6107312A (en)	2000-08-22	Thiopyridines for use in the control of helicobacter bacteria
US5922720A (en)	1999-07-13	Piperazinothiopyridines for the control of Helicobacter bacteria
US20040158066A1 (en)	2004-08-12	Novel pyridylmethylaminopyrimidines
PL178477B1 (pl)	2000-05-31	Nowe związki, pochodne arylotioalkilotiopirydyny, oraz sposób ich wytwarzania i lek zawierający te związki
MXPA99005858A (en)	2000-01-01	Imidazopyridazines
AU2002314064A1 (en)	2002-12-03	Novel pyridylmethylaminopyrimidines