SK14912000A3 - Imidazopyridínové deriváty, ktoré inhibujú vylučovanie žalúdočnej kyseliny, spôsob ich prípravy, medziprodukty tohto spôsobu a farmaceutická formulácia - Google Patents

Imidazopyridínové deriváty, ktoré inhibujú vylučovanie žalúdočnej kyseliny, spôsob ich prípravy, medziprodukty tohto spôsobu a farmaceutická formulácia Download PDF

Info

Publication number: SK14912000A3
Authority: SK; Slovakia
Prior art keywords: alkyl; compound; formula; ethyl; alkoxy
Prior art date: 1998-04-29

Application number

SK1491-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Kosrat Amin

Mikael Dahlstrm

Peter Nordberg

Ingemar Starke

Original Assignee

Astrazeneca Ab

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.)

1998-04-29

Filing date

1999-04-23

Publication date

2001-06-11

1999-04-23 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2001-06-11 Publication of SK14912000A3 publication Critical patent/SK14912000A3/sk

Links

230000027119 gastric acid secretion Effects 0.000 title claims description 9
125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 147
-1 nitro, amino Chemical group 0.000 claims description 40
229910052736 halogen Inorganic materials 0.000 claims description 31
150000002367 halogens Chemical class 0.000 claims description 31
229910052757 nitrogen Inorganic materials 0.000 claims description 29
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
125000003118 aryl group Chemical group 0.000 claims description 25
229910052739 hydrogen Inorganic materials 0.000 claims description 25
125000001424 substituent group Chemical group 0.000 claims description 25
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
239000012442 inert solvent Substances 0.000 claims description 18
238000002360 preparation method Methods 0.000 claims description 18
229910052799 carbon Inorganic materials 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 16
125000001041 indolyl group Chemical group 0.000 claims description 15
125000001624 naphthyl group Chemical group 0.000 claims description 15
125000004076 pyridyl group Chemical group 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 15
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 14
239000004480 active ingredient Substances 0.000 claims description 14
125000002883 imidazolyl group Chemical group 0.000 claims description 14
238000011282 treatment Methods 0.000 claims description 13
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 12
238000000034 method Methods 0.000 claims description 12
LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 10
239000008194 pharmaceutical composition Substances 0.000 claims description 10
125000002541 furyl group Chemical group 0.000 claims description 9
125000001544 thienyl group Chemical group 0.000 claims description 9
208000017189 Gastrointestinal inflammatory disease Diseases 0.000 claims description 8
125000004185 ester group Chemical group 0.000 claims description 8
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
230000008569 process Effects 0.000 claims description 7
NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
230000002401 inhibitory effect Effects 0.000 claims description 6
230000005764 inhibitory process Effects 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
239000004599 antimicrobial Substances 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
125000005842 heteroatom Chemical group 0.000 claims description 5
125000002757 morpholinyl group Chemical group 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
125000003386 piperidinyl group Chemical group 0.000 claims description 5
229920006395 saturated elastomer Polymers 0.000 claims description 5
241000590002 Helicobacter pylori Species 0.000 claims description 4
241000124008 Mammalia Species 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
210000001156 gastric mucosa Anatomy 0.000 claims description 4
229940037467 helicobacter pylori Drugs 0.000 claims description 4
208000015181 infectious disease Diseases 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
230000002265 prevention Effects 0.000 claims description 4
238000011321 prophylaxis Methods 0.000 claims description 4
ZYIBSYLOZXPIFU-QFIPXVFZSA-N (2s)-1-[8-[(2-ethyl-6-methylphenyl)methylamino]-2,3-dimethylimidazo[1,2-a]pyridine-6-carbonyl]pyrrolidine-2-carboxamide Chemical compound CCC1=CC=CC(C)=C1CNC1=CC(C(=O)N2[C@@H](CCC2)C(N)=O)=CN2C1=NC(C)=C2C ZYIBSYLOZXPIFU-QFIPXVFZSA-N 0.000 claims description 3
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 3
FGSCZMLSHATKFV-UHFFFAOYSA-N [8-[(2-ethyl-6-methylphenyl)methylamino]-2,3-dimethylimidazo[1,2-a]pyridin-6-yl]-morpholin-4-ylmethanone Chemical compound CCC1=CC=CC(C)=C1CNC1=CC(C(=O)N2CCOCC2)=CN2C1=NC(C)=C2C FGSCZMLSHATKFV-UHFFFAOYSA-N 0.000 claims description 3
150000001408 amides Chemical class 0.000 claims description 3
229910021529 ammonia Inorganic materials 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 3
AFXWDWGDRAFKLH-UHFFFAOYSA-N n-(4-ethoxyphenyl)-8-[(2-ethyl-6-methylphenyl)methylamino]-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound C1=CC(OCC)=CC=C1NC(=O)C1=CN2C(C)=C(C)N=C2C(NCC=2C(=CC=CC=2C)CC)=C1 AFXWDWGDRAFKLH-UHFFFAOYSA-N 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
238000002560 therapeutic procedure Methods 0.000 claims description 3
MCBFKBNKDJQUSI-UHFFFAOYSA-N 4-[2-[[8-[(2-ethyl-6-methylphenyl)methylamino]-2,3-dimethylimidazo[1,2-a]pyridine-6-carbonyl]amino]ethoxy]-4-oxobutanoic acid Chemical compound CCC1=CC=CC(C)=C1CNC1=CC(C(=O)NCCOC(=O)CCC(O)=O)=CN2C1=NC(C)=C2C MCBFKBNKDJQUSI-UHFFFAOYSA-N 0.000 claims description 2
GAEHPIKXJDYKOI-UHFFFAOYSA-N 5-[(2-ethyl-6-methylphenyl)methylamino]-n-[2-(2-hydroxyethoxy)ethyl]-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound CCC1=CC=CC(C)=C1CNC1=C(C(=O)NCCOCCO)C=CC2=NC(C)=C(C)N12 GAEHPIKXJDYKOI-UHFFFAOYSA-N 0.000 claims description 2
YOHSQJGHDLKCKI-UHFFFAOYSA-N 8-[(2-ethyl-6-methylphenyl)methylamino]-n-hydroxy-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound CCC1=CC=CC(C)=C1CNC1=CC(C(=O)NO)=CN2C1=NC(C)=C2C YOHSQJGHDLKCKI-UHFFFAOYSA-N 0.000 claims description 2
YJLWIWGVSSBEIG-UHFFFAOYSA-N [5-[(2-ethyl-6-methylphenyl)methylamino]-3-(hydroxymethyl)-2-methylimidazo[1,2-a]pyridin-6-yl]-morpholin-4-ylmethanone Chemical compound C(C)C1=C(CNC2=C(C=CC=3N2C(=C(N=3)C)CO)C(=O)N2CCOCC2)C(=CC=C1)C YJLWIWGVSSBEIG-UHFFFAOYSA-N 0.000 claims description 2
WHDWGIAUXIFZDU-UHFFFAOYSA-N [8-[(2-ethyl-6-methylphenyl)methylamino]-2,3-dimethylimidazo[1,2-a]pyridin-6-yl]-(3-hydroxypyrrolidin-1-yl)methanone Chemical compound CCC1=CC=CC(C)=C1CNC1=CC(C(=O)N2CC(O)CC2)=CN2C1=NC(C)=C2C WHDWGIAUXIFZDU-UHFFFAOYSA-N 0.000 claims description 2
239000007822 coupling agent Substances 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
KYHYBKLJALARJB-UHFFFAOYSA-N n-[2-(3,4-dihydroxyphenyl)ethyl]-8-[(2-ethyl-6-methylphenyl)methylamino]-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound CCC1=CC=CC(C)=C1CNC1=CC(C(=O)NCCC=2C=C(O)C(O)=CC=2)=CN2C1=NC(C)=C2C KYHYBKLJALARJB-UHFFFAOYSA-N 0.000 claims description 2
OLUJVOMKPMVNPO-UHFFFAOYSA-N n-[2-(dimethylamino)-2-oxoethyl]-8-[(2-ethyl-6-methylphenyl)methylamino]-n,2,3-trimethylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound CCC1=CC=CC(C)=C1CNC1=CC(C(=O)N(C)CC(=O)N(C)C)=CN2C1=NC(C)=C2C OLUJVOMKPMVNPO-UHFFFAOYSA-N 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
206010009944 Colon cancer Diseases 0.000 claims 1
ZTDZEZIHAZFOPK-UHFFFAOYSA-N [8-[(2-ethyl-6-methylphenyl)methylamino]-2,3-dimethylimidazo[1,2-a]pyridin-5-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound CCC1=CC=CC(C)=C1CNC(C1=NC(C)=C(C)N11)=CC=C1C(=O)N1CCN(C)CC1 ZTDZEZIHAZFOPK-UHFFFAOYSA-N 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
239000003153 chemical reaction reagent Substances 0.000 claims 1
230000008878 coupling Effects 0.000 claims 1
238000010168 coupling process Methods 0.000 claims 1
238000005859 coupling reaction Methods 0.000 claims 1
230000007062 hydrolysis Effects 0.000 claims 1
238000006460 hydrolysis reaction Methods 0.000 claims 1
229940126409 proton pump inhibitor Drugs 0.000 claims 1
239000000612 proton pump inhibitor Substances 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
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238000005160 1H NMR spectroscopy Methods 0.000 description 18
238000012360 testing method Methods 0.000 description 16
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CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 14
239000002904 solvent Substances 0.000 description 14
239000012317 TBTU Substances 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
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239000000243 solution Substances 0.000 description 11
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HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
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238000001802 infusion Methods 0.000 description 3
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IDYZIJYBMGIQMJ-UHFFFAOYSA-N enoxacin Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 IDYZIJYBMGIQMJ-UHFFFAOYSA-N 0.000 description 1
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MVPICKVDHDWCJQ-UHFFFAOYSA-N ethyl 3-pyrrolidin-1-ylpropanoate Chemical compound CCOC(=O)CCN1CCCC1 MVPICKVDHDWCJQ-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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150000002431 hydrogen Chemical class 0.000 description 1
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229930182823 kanamycin A Natural products 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
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MJIHNNLFOKEZEW-UHFFFAOYSA-N lansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1 MJIHNNLFOKEZEW-UHFFFAOYSA-N 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000003120 macrolide antibiotic agent Substances 0.000 description 1
229940041033 macrolides Drugs 0.000 description 1
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239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
229940031958 magnesium carbonate hydroxide Drugs 0.000 description 1
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
239000000347 magnesium hydroxide Substances 0.000 description 1
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229960000816 magnesium hydroxide Drugs 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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235000011090 malic acid Nutrition 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
210000004379 membrane Anatomy 0.000 description 1
239000012528 membrane Substances 0.000 description 1
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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
125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 description 1
229960004085 mosapride Drugs 0.000 description 1
CAGXPPQTXUCBOY-UHFFFAOYSA-N n,n-dimethyl-2-(methylamino)acetamide Chemical compound CNCC(=O)N(C)C CAGXPPQTXUCBOY-UHFFFAOYSA-N 0.000 description 1
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PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 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
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
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150000007524 organic acids Chemical class 0.000 description 1
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239000000843 powder Substances 0.000 description 1
238000002953 preparative HPLC Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
150000007660 quinolones Chemical class 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
238000011552 rat model Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
238000005070 sampling Methods 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
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229940045902 sodium stearyl fumarate Drugs 0.000 description 1
238000013223 sprague-dawley female rat Methods 0.000 description 1
238000012453 sprague-dawley rat model Methods 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
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235000019698 starch Nutrition 0.000 description 1
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150000005846 sugar alcohols Chemical class 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
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229940040944 tetracyclines Drugs 0.000 description 1
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239000002562 thickening agent Substances 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
230000036269 ulceration Effects 0.000 description 1
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239000001993 wax Substances 0.000 description 1
239000002132 β-lactam antibiotic Substances 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—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
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nutrition Science (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SK1491-2000A 1998-04-29 1999-04-23 Imidazopyridínové deriváty, ktoré inhibujú vylučovanie žalúdočnej kyseliny, spôsob ich prípravy, medziprodukty tohto spôsobu a farmaceutická formulácia SK14912000A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
SE9801526A SE9801526D0 (sv)	1998-04-29	1998-04-29	New compounds
PCT/SE1999/000662 WO1999055705A1 (fr)	1998-04-29	1999-04-23	Derives d'imidazo pyridine qui inhibent la secretion d'acide gastrique

Publications (1)

Publication Number	Publication Date
SK14912000A3 true SK14912000A3 (sk)	2001-06-11

Family

ID=20411154

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
SK1491-2000A SK14912000A3 (sk)	1998-04-29	1999-04-23	Imidazopyridínové deriváty, ktoré inhibujú vylučovanie žalúdočnej kyseliny, spôsob ich prípravy, medziprodukty tohto spôsobu a farmaceutická formulácia
SK1492-2000A SK285768B6 (sk)	1998-04-29	1999-04-23	Imidazopyridínové deriváty inhibujúce vylučovaniežalúdočnej kyseliny, spôsob ich prípravy, farmaceutický prostriedok a ich použitie

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
SK1492-2000A SK285768B6 (sk)	1998-04-29	1999-04-23	Imidazopyridínové deriváty inhibujúce vylučovaniežalúdočnej kyseliny, spôsob ich prípravy, farmaceutický prostriedok a ich použitie

Country Status (33)

Country	Link
US (2)	US6313137B1 (fr)
EP (4)	EP1491543B1 (fr)
JP (2)	JP3883383B2 (fr)
KR (3)	KR100595806B1 (fr)
CN (2)	CN1174980C (fr)
AR (2)	AR015769A1 (fr)
AT (4)	ATE372339T1 (fr)
AU (2)	AU769190B2 (fr)
BR (2)	BR9909996B1 (fr)
CA (2)	CA2329922C (fr)
CZ (2)	CZ292567B6 (fr)
DE (4)	DE69937077T2 (fr)
DK (2)	DK1073657T3 (fr)
EE (2)	EE04676B1 (fr)
ES (2)	ES2249913T3 (fr)
HU (2)	HUP0102425A3 (fr)
ID (2)	ID26819A (fr)
IL (4)	IL139297A0 (fr)
IS (2)	IS5684A (fr)
MY (2)	MY121389A (fr)
NO (2)	NO317262B1 (fr)
NZ (2)	NZ507638A (fr)
PL (2)	PL343797A1 (fr)
RU (2)	RU2235725C2 (fr)
SA (2)	SA99200064B1 (fr)
SE (1)	SE9801526D0 (fr)
SI (1)	SI1073656T1 (fr)
SK (2)	SK14912000A3 (fr)
TR (4)	TR200003176T2 (fr)
TW (2)	TW490466B (fr)
UA (2)	UA67769C2 (fr)
WO (2)	WO1999055705A1 (fr)
ZA (2)	ZA200005797B (fr)

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US6489346B1 (en)	1996-01-04	2002-12-03	The Curators Of The University Of Missouri	Substituted benzimidazole dosage forms and method of using same
SE9802794D0 (sv) *	1998-08-21	1998-08-21	Astra Ab	New compounds
SE0003186D0 (sv)	2000-09-07	2000-09-07	Astrazeneca Ab	New process
US6900324B2 (en)	2000-09-07	2005-05-31	Astrazeneca Ab	Process for preparing a substituted imidazopyridine compound
UA80393C2 (uk)	2000-12-07	2007-09-25	Алтана Фарма Аг	Фармацевтична композиція, яка містить інгібітор фде 4, диспергований в матриці
SE0100295D0 (sv) *	2001-02-01	2001-02-01	Astrazeneca Ab	New compounds
SE0100297D0 (sv) *	2001-02-01	2001-02-01	Astrazeneca Ab	New compounds
SE0100296D0 (sv) *	2001-02-01	2001-02-01	Astrazeneca Ab	New compounds
EP1361868A1 (fr) *	2001-02-13	2003-11-19	AstraZeneca AB	Nouvelle preparation a liberation modifiee
CZ20032398A3 (cs) *	2001-03-08	2004-02-18	Astrazeneca Ab	Nové použití derivátů 6-karboxamidoimidazo [1,2-a] pyridinu
SE0102808D0 (sv) *	2001-08-22	2001-08-22	Astrazeneca Ab	New compounds
MY140561A (en)	2002-02-20	2009-12-31	Nycomed Gmbh	Dosage form containing pde 4 inhibitor as active ingredient
SE0201940D0 (sv) *	2002-06-20	2002-06-20	Astrazeneca Ab	New combination II
SE0201939D0 (sv) *	2002-06-20	2002-06-20	Astrazeneca Ab	New combination
EP1539756B1 (fr)	2002-09-19	2007-11-14	Schering Corporation	Imidazopyridines utilisees comme inhibiteurs des kinases dependantes des cyclines
WO2004046144A1 (fr)	2002-11-19	2004-06-03	Altana Pharma Ag	Imidazopyridines substituees en position 8
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SE525349C2 (sv) *	2003-06-23	2005-02-08	Volvo Penta Ab	Utombordsdrev för båtar
SE0301904D0 (sv)	2003-06-26	2003-06-26	Astrazeneca Ab	Novel imidazopyridine compound II with therapeutic effect
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SE0303451D0 (sv) *	2003-12-18	2003-12-18	Astrazeneca Ab	New compounds
EP1711498A2 (fr) *	2004-01-26	2006-10-18	Altana Pharma AG	1,2,4-triazolo¬1,5-a\|pyridines inhibant la secretion d'acide gastrique
US8906940B2 (en)	2004-05-25	2014-12-09	Santarus, Inc.	Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them
EA011512B1 (ru) *	2004-12-17	2009-04-28	Ракуалиа Фарма Инк.	Производные хромана, полезные в качестве антагонистов кислотной помпы
US8663694B2 (en)	2005-03-16	2014-03-04	Takeda Gmbh	Taste masked dosage form containing roflumilast
MX2007011710A (es) *	2005-03-21	2007-11-20	S Bio Pte Ltd	Derivados de imidazo[1,2-a]piridina, preparacion y aplicaciones farmaceuticas.
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SI1959955T1 (sl)	2005-12-05	2011-02-28	Pfizer Prod Inc	Postopek zdravljenja abnormalne celične rasti
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1998
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Also Published As

Publication number	Publication date
NZ507638A (en)	2003-10-31
KR100595805B1 (ko)	2006-07-03
EP1491543A1 (fr)	2004-12-29
CZ292567B6 (cs)	2003-10-15
DE69937077T2 (de)	2008-05-29
MY121389A (en)	2006-01-28
TR200102728T2 (tr)	2002-06-21
ES2252975T3 (es)	2006-05-16
HUP0102313A3 (en)	2002-10-28
EP1073657B1 (fr)	2005-12-07
AU769108B2 (en)	2004-01-15
DE69928792D1 (de)	2006-01-12
ID26819A (id)	2001-02-15
KR100650472B1 (ko)	2006-11-28
MY121379A (en)	2006-01-28
CN1165535C (zh)	2004-09-08
CA2329922A1 (fr)	1999-11-04
ATE372340T1 (de)	2007-09-15
PL343797A1 (en)	2001-09-10
DE69927803D1 (de)	2006-03-02
NO318203B1 (no)	2005-02-14
SI1073656T1 (sl)	2006-02-28
WO1999055706A1 (fr)	1999-11-04
DK1073656T3 (da)	2006-01-16
TR200102612T2 (tr)	2002-06-21
IL139297A (en)	2007-06-03
HUP0102313A2 (hu)	2001-12-28
ES2249913T3 (es)	2006-04-01
DK1073657T3 (da)	2006-03-13
AR015769A1 (es)	2001-05-16
JP2002513025A (ja)	2002-05-08
NO20005451L (no)	2000-12-27
SK14922000A3 (sk)	2001-06-11
SE9801526D0 (sv)	1998-04-29
JP2002513024A (ja)	2002-05-08
EP1491542A2 (fr)	2004-12-29
ZA200005797B (en)	2002-01-18
WO1999055706A9 (fr)	2000-03-16
CN1307577A (zh)	2001-08-08
KR20010043133A (ko)	2001-05-25
KR100595806B1 (ko)	2006-07-03
JP3692034B2 (ja)	2005-09-07
HUP0102425A3 (en)	2002-12-28
HK1033317A1 (en)	2001-08-24
WO1999055705A1 (fr)	1999-11-04
TR200003176T2 (tr)	2001-03-21
US6313137B1 (en)	2001-11-06
ATE307130T1 (de)	2005-11-15
EE200000626A (et)	2002-04-15
DE69937077D1 (de)	2007-10-18
CN1174980C (zh)	2004-11-10
EE04916B1 (et)	2007-10-15
AU4300699A (en)	1999-11-16
UA67769C2 (uk)	2004-07-15
AU4300799A (en)	1999-11-16
EP1073656B1 (fr)	2005-10-19
SA99200065A (ar)	2005-12-03
CZ293977B6 (cs)	2004-09-15
NO20005451D0 (no)	2000-10-27
NO20005450D0 (no)	2000-10-27
TW490466B (en)	2002-06-11
SA99200065B1 (ar)	2006-11-07
TR200003149T2 (tr)	2001-03-21
RU2238271C2 (ru)	2004-10-20
EP1491543B1 (fr)	2007-09-05
DE69928792T2 (de)	2006-07-20
EP1073656A1 (fr)	2001-02-07
SA99200064B1 (ar)	2006-10-11
KR20050121760A (ko)	2005-12-27
US6313136B1 (en)	2001-11-06
NO317262B1 (no)	2004-09-27
CA2329921A1 (fr)	1999-11-04
CA2329922C (fr)	2006-04-11
KR20010043134A (ko)	2001-05-25
BR9909995A (pt)	2000-12-26
ZA200005796B (en)	2002-01-18
DE69927803T2 (de)	2006-07-06
HK1071139A1 (en)	2005-07-08
HK1036981A1 (en)	2002-01-25
PL343801A1 (en)	2001-09-10
HK1036984A1 (en)	2002-01-25
PL195000B1 (pl)	2007-07-31
RU2235725C2 (ru)	2004-09-10
IL139200A (en)	2010-04-29
EP1073657A1 (fr)	2001-02-07
EP1491542A3 (fr)	2005-01-05
EE200000664A (et)	2002-04-15
IL139297A0 (en)	2001-11-25
IS5684A (is)	2000-10-25
DE69937076T2 (de)	2008-05-29
ATE372339T1 (de)	2007-09-15
JP3883383B2 (ja)	2007-02-21
CZ20003982A3 (cs)	2001-02-14
CN1306533A (zh)	2001-08-01
NO20005450L (no)	2000-12-22
BR9909996A (pt)	2000-12-26
AU769190B2 (en)	2004-01-22
BR9909995B1 (pt)	2010-07-13
BR9909996B1 (pt)	2010-08-24
SK285768B6 (sk)	2007-07-06
NZ507639A (en)	2004-01-30
ATE312101T1 (de)	2005-12-15
EP1491542B1 (fr)	2007-09-05
TWI250159B (en)	2006-03-01
IS5683A (is)	2000-10-25
ID27530A (id)	2001-04-12
DE69937076D1 (de)	2007-10-18
EE04676B1 (et)	2006-08-15
AR015768A1 (es)	2001-05-16
UA66846C2 (uk)	2004-06-15
HUP0102425A2 (hu)	2001-11-28
CZ20003981A3 (cs)	2001-03-14
IL139200A0 (en)	2001-11-25
HK1033457A1 (en)	2001-08-31

Publication	Publication Date	Title
SK14912000A3 (sk)	2001-06-11	Imidazopyridínové deriváty, ktoré inhibujú vylučovanie žalúdočnej kyseliny, spôsob ich prípravy, medziprodukty tohto spôsobu a farmaceutická formulácia
SK283903B6 (sk)	2004-04-06	Substituované imidazopyridínové deriváty na inhibíciu sekrécie žalúdočnej kyseliny, spôsob ich prípravy, farmaceutické kompozície s ich obsahom a ich použitie
NZ531110A (en)	2005-10-28	Novel imidazopyridine compounds with therapeutic effect
HK1033457B (en)	2006-04-07	Imidazo pyridine derivatives which inhibit gastric acid secretion
MXPA00010231A (en)	2002-05-09	Imidazo pyridine derivatives which inhibit gastric acid secretion
HK1033317B (en)	2006-06-30	Imidazo pyridine derivatives which inhibit gastric acid secretion
MXPA00010239A (en)	2001-07-31	Imidazo pyridine derivatives which inhibit gastric acid secretion