NO317262B1 - Imidazopyridinderivater som inhiberer magesyresekresjon, farmasoytisk formulering som inneholder slike derivater, fremgangsmate for deres fremstilling, anvendelse derav, og mellomprodukter. - Google Patents

Imidazopyridinderivater som inhiberer magesyresekresjon, farmasoytisk formulering som inneholder slike derivater, fremgangsmate for deres fremstilling, anvendelse derav, og mellomprodukter. Download PDF

Info

Publication number: NO317262B1
Authority: NO; Norway
Prior art keywords: compound; formula; pyridine; carboxamide; dimethyl
Prior art date: 1998-04-29

Application number

NO20005450A

Other languages

English (en)

Norwegian (no)

Other versions

NO20005450D0 (no

NO20005450L (no

Inventor

Ingemar Starke

Kosrat Amin

Peter Nordberg

Michael Dahlstrom

Original Assignee

Astrazeneca Ab Global Ip

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

2000-10-27

Publication date

2004-09-27

2000-10-27 Application filed by Astrazeneca Ab Global Ip filed Critical Astrazeneca Ab Global Ip

2000-10-27 Publication of NO20005450D0 publication Critical patent/NO20005450D0/no

2000-12-22 Publication of NO20005450L publication Critical patent/NO20005450L/no

2004-09-27 Publication of NO317262B1 publication Critical patent/NO317262B1/no

Links

238000002360 preparation method Methods 0.000 title claims description 26
238000000034 method Methods 0.000 title claims description 18
230000027119 gastric acid secretion Effects 0.000 title claims description 11
239000008194 pharmaceutical composition Substances 0.000 title claims description 10
230000008569 process Effects 0.000 title claims description 7
239000000543 intermediate Substances 0.000 title description 3
125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 191
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
238000006243 chemical reaction Methods 0.000 claims description 30
239000012442 inert solvent Substances 0.000 claims description 23
-1 2,3-dimethyl-8-(2,6-dimethylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxamide 2,3-dimethyl-8-(2-ethyl-4-fluoro-6-methylbenzylamino) -imidazo[1,2-a]pyridine-6- carboxamide Chemical compound 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 20
238000011282 treatment Methods 0.000 claims description 18
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 12
230000005764 inhibitory process Effects 0.000 claims description 11
238000004519 manufacturing process Methods 0.000 claims description 11
239000004480 active ingredient Substances 0.000 claims description 10
125000004185 ester group Chemical group 0.000 claims description 10
208000017189 Gastrointestinal inflammatory disease Diseases 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 9
229910021529 ammonia Inorganic materials 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
210000001156 gastric mucosa Anatomy 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
230000002401 inhibitory effect Effects 0.000 claims description 6
230000009467 reduction Effects 0.000 claims description 6
239000004599 antimicrobial Substances 0.000 claims description 5
GHVIMBCFLRTFHI-UHFFFAOYSA-N 8-[(2,6-dimethylphenyl)methylamino]-n-(2-hydroxyethyl)-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound C=1C(C(=O)NCCO)=CN2C(C)=C(C)N=C2C=1NCC1=C(C)C=CC=C1C GHVIMBCFLRTFHI-UHFFFAOYSA-N 0.000 claims description 4
IDSZXCFCCNVXER-UHFFFAOYSA-N 8-[(2-ethyl-6-methylphenyl)methylamino]-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound CCC1=CC=CC(C)=C1CNC1=CC(C(N)=O)=CN2C1=NC(C)=C2C IDSZXCFCCNVXER-UHFFFAOYSA-N 0.000 claims description 4
241000124008 Mammalia Species 0.000 claims description 4
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 4
208000015181 infectious disease Diseases 0.000 claims description 4
230000002265 prevention Effects 0.000 claims description 4
238000011321 prophylaxis Methods 0.000 claims description 4
XFELTQZYMQLCDH-UHFFFAOYSA-N 2,3-dimethyl-8-[(2-methylphenyl)methylamino]imidazo[1,2-a]pyridine-6-carboxamide Chemical compound C=1C(C(N)=O)=CN2C(C)=C(C)N=C2C=1NCC1=CC=CC=C1C XFELTQZYMQLCDH-UHFFFAOYSA-N 0.000 claims description 3
UNQLORILSMOXOU-UHFFFAOYSA-N 8-[(2,6-diethylphenyl)methylamino]-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound CCC1=CC=CC(CC)=C1CNC1=CC(C(N)=O)=CN2C1=NC(C)=C2C UNQLORILSMOXOU-UHFFFAOYSA-N 0.000 claims description 3
MUDJXGVFMYNBMY-UHFFFAOYSA-N 8-[(2,6-dimethylphenyl)methylamino]-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound C=1C(C(N)=O)=CN2C(C)=C(C)N=C2C=1NCC1=C(C)C=CC=C1C MUDJXGVFMYNBMY-UHFFFAOYSA-N 0.000 claims description 3
CLUFEHKNBCKOTD-UHFFFAOYSA-N 8-[(2-ethyl-4-fluoro-6-methylphenyl)methylamino]-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide;methanesulfonic acid Chemical compound CS(O)(=O)=O.CCC1=CC(F)=CC(C)=C1CNC1=CC(C(N)=O)=CN2C1=NC(C)=C2C CLUFEHKNBCKOTD-UHFFFAOYSA-N 0.000 claims description 3
FNHKSNKIKUYVDM-UHFFFAOYSA-N 8-[(2-ethyl-6-methylphenyl)methylamino]-n,n,2,3-tetramethylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound CCC1=CC=CC(C)=C1CNC1=CC(C(=O)N(C)C)=CN2C1=NC(C)=C2C FNHKSNKIKUYVDM-UHFFFAOYSA-N 0.000 claims description 3
CSJLZSZWYHFDCR-UHFFFAOYSA-N 8-[(2-ethyl-6-methylphenyl)methylamino]-n-(2-methoxyethyl)-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound CCC1=CC=CC(C)=C1CNC1=CC(C(=O)NCCOC)=CN2C1=NC(C)=C2C CSJLZSZWYHFDCR-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
238000002560 therapeutic procedure Methods 0.000 claims description 3
WMFAXRSCKYBOJR-UHFFFAOYSA-N 8-[(2-bromo-6-methylphenyl)methylamino]-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound C=1C(C(N)=O)=CN2C(C)=C(C)N=C2C=1NCC1=C(C)C=CC=C1Br WMFAXRSCKYBOJR-UHFFFAOYSA-N 0.000 claims description 2
CLXRWZQVJIZKBC-UHFFFAOYSA-N 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)NC)=CN2C1=NC(C)=C2C CLXRWZQVJIZKBC-UHFFFAOYSA-N 0.000 claims description 2
IQVAZCKILWGSFS-UHFFFAOYSA-N 8-[(2-ethylphenyl)methylamino]-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound CCC1=CC=CC=C1CNC1=CC(C(N)=O)=CN2C1=NC(C)=C2C IQVAZCKILWGSFS-UHFFFAOYSA-N 0.000 claims description 2
239000003153 chemical reaction reagent Substances 0.000 claims description 2
230000008878 coupling Effects 0.000 claims description 2
238000010168 coupling process Methods 0.000 claims description 2
238000005859 coupling reaction Methods 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
150000003840 hydrochlorides Chemical class 0.000 claims description 2
IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims description 2
CKAMGCWTONYLBM-UHFFFAOYSA-N 8-[(2-ethyl-6-methylphenyl)methylamino]-3-(hydroxymethyl)-2-methylimidazo[1,2-a]pyridine-6-carboxamide Chemical group CCC1=CC=CC(C)=C1CNC1=CC(C(N)=O)=CN2C1=NC(C)=C2CO CKAMGCWTONYLBM-UHFFFAOYSA-N 0.000 claims 1
FTXBKPOSKGLYOM-UHFFFAOYSA-N 8-[(2-ethyl-6-methylphenyl)methylamino]-n,n-bis(2-hydroxyethyl)-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound CCC1=CC=CC(C)=C1CNC1=CC(C(=O)N(CCO)CCO)=CN2C1=NC(C)=C2C FTXBKPOSKGLYOM-UHFFFAOYSA-N 0.000 claims 1
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
229940126409 proton pump inhibitor Drugs 0.000 claims 1
239000000612 proton pump inhibitor Substances 0.000 claims 1
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 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 150
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 105
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 65
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
239000002904 solvent Substances 0.000 description 30
239000000741 silica gel Substances 0.000 description 28
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IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 18
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NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 15
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230000000694 effects Effects 0.000 description 13
238000005160 1H NMR spectroscopy Methods 0.000 description 11
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238000002425 crystallisation Methods 0.000 description 6
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HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
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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
229960001180 norfloxacin Drugs 0.000 description 1
229960000381 omeprazole Drugs 0.000 description 1
150000007524 organic acids Chemical class 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
239000008188 pellet Substances 0.000 description 1
ANRIQLNBZQLTFV-DZUOILHNSA-N pentagastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1[C]2C=CC=CC2=NC=1)NC(=O)CCNC(=O)OC(C)(C)C)CCSC)C(N)=O)C1=CC=CC=C1 ANRIQLNBZQLTFV-DZUOILHNSA-N 0.000 description 1
229960000444 pentagastrin Drugs 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
208000000689 peptic esophagitis Diseases 0.000 description 1
208000011906 peptic ulcer disease Diseases 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
230000036470 plasma concentration Effects 0.000 description 1
239000011591 potassium Substances 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
235000019260 propionic acid Nutrition 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
239000000376 reactant Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000011160 research Methods 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
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
229940045902 sodium stearyl fumarate Drugs 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
150000005846 sugar alcohols Chemical class 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 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
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
229960002180 tetracycline Drugs 0.000 description 1
229930101283 tetracycline Natural products 0.000 description 1
229940040944 tetracyclines Drugs 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
238000004448 titration Methods 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
230000001960 triggered effect Effects 0.000 description 1
230000036269 ulceration Effects 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
239000002132 β-lactam antibiotic Substances 0.000 description 1
229940124586 β-lactam antibiotics Drugs 0.000 description 1

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)

NO20005450A 1998-04-29 2000-10-27 Imidazopyridinderivater som inhiberer magesyresekresjon, farmasoytisk formulering som inneholder slike derivater, fremgangsmate for deres fremstilling, anvendelse derav, og mellomprodukter. NO317262B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
SE9801526A SE9801526D0 (sv)	1998-04-29	1998-04-29	New compounds
PCT/SE1999/000663 WO1999055706A1 (en)	1998-04-29	1999-04-23	Imidazo pyridine derivatives which inhibit gastric acid secretion

Publications (3)

Publication Number	Publication Date
NO20005450D0 NO20005450D0 (no)	2000-10-27
NO20005450L NO20005450L (no)	2000-12-22
NO317262B1 true NO317262B1 (no)	2004-09-27

Family

ID=20411154

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
NO20005450A NO317262B1 (no)	1998-04-29	2000-10-27	Imidazopyridinderivater som inhiberer magesyresekresjon, farmasoytisk formulering som inneholder slike derivater, fremgangsmate for deres fremstilling, anvendelse derav, og mellomprodukter.
NO20005451A NO318203B1 (no)	1998-04-29	2000-10-27	Imidazopyridinderivater som inhiberer magesyresekresjon

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
NO20005451A NO318203B1 (no)	1998-04-29	2000-10-27	Imidazopyridinderivater som inhiberer magesyresekresjon

Country Status (34)

Country	Link
US (2)	US6313137B1 (sk)
EP (4)	EP1073657B1 (sk)
JP (2)	JP3692034B2 (sk)
KR (3)	KR100650472B1 (sk)
CN (2)	CN1174980C (sk)
AR (2)	AR015768A1 (sk)
AT (4)	ATE312101T1 (sk)
AU (2)	AU769190B2 (sk)
BR (2)	BR9909996B1 (sk)
CA (2)	CA2329921A1 (sk)
CZ (2)	CZ292567B6 (sk)
DE (4)	DE69937076T2 (sk)
DK (2)	DK1073657T3 (sk)
EE (2)	EE04916B1 (sk)
ES (2)	ES2249913T3 (sk)
HK (5)	HK1033457A1 (sk)
HU (2)	HUP0102313A3 (sk)
ID (2)	ID27530A (sk)
IL (4)	IL139200A0 (sk)
IS (2)	IS5683A (sk)
MY (2)	MY121379A (sk)
NO (2)	NO317262B1 (sk)
NZ (2)	NZ507638A (sk)
PL (2)	PL195000B1 (sk)
RU (2)	RU2238271C2 (sk)
SA (2)	SA99200065B1 (sk)
SE (1)	SE9801526D0 (sk)
SI (1)	SI1073656T1 (sk)
SK (2)	SK14912000A3 (sk)
TR (4)	TR200003176T2 (sk)
TW (2)	TWI250159B (sk)
UA (2)	UA67769C2 (sk)
WO (2)	WO1999055705A1 (sk)
ZA (2)	ZA200005797B (sk)

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1998
- 1998-04-29 SE SE9801526A patent/SE9801526D0/xx unknown
1999
- 1999-04-16 AR ARP990101776A patent/AR015768A1/es active IP Right Grant
- 1999-04-16 TW TW088106128A patent/TWI250159B/zh not_active IP Right Cessation
- 1999-04-16 AR ARP990101777A patent/AR015769A1/es active IP Right Grant
- 1999-04-16 TW TW088106129A patent/TW490466B/zh not_active IP Right Cessation
- 1999-04-23 KR KR1020007012028A patent/KR100650472B1/ko not_active IP Right Cessation
- 1999-04-23 EP EP99947038A patent/EP1073657B1/en not_active Expired - Lifetime
- 1999-04-23 TR TR2000/03176T patent/TR200003176T2/xx unknown
- 1999-04-23 PL PL343801A patent/PL195000B1/pl not_active IP Right Cessation
- 1999-04-23 PL PL99343797A patent/PL343797A1/xx unknown
- 1999-04-23 JP JP2000545865A patent/JP3692034B2/ja not_active Expired - Fee Related
- 1999-04-23 ID IDW20002205A patent/ID27530A/id unknown
- 1999-04-23 HU HU0102313A patent/HUP0102313A3/hu unknown
- 1999-04-23 ES ES99947037T patent/ES2249913T3/es not_active Expired - Lifetime
- 1999-04-23 AT AT99947038T patent/ATE312101T1/de not_active IP Right Cessation
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- 1999-04-23 RU RU2000127019/04A patent/RU2238271C2/ru active
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- 1999-04-23 TR TR2000/03149T patent/TR200003149T2/xx unknown
- 1999-04-23 WO PCT/SE1999/000662 patent/WO1999055705A1/en not_active Application Discontinuation
- 1999-04-23 EE EEP200000664A patent/EE04916B1/xx not_active IP Right Cessation
- 1999-04-23 DE DE69927803T patent/DE69927803T2/de not_active Expired - Lifetime
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- 1999-04-23 KR KR1020057022787A patent/KR100595805B1/ko not_active IP Right Cessation
- 1999-04-23 CN CNB998077992A patent/CN1174980C/zh not_active Expired - Fee Related
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- 1999-04-23 UA UA2000106034A patent/UA66846C2/uk unknown
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- 1999-04-23 NZ NZ507639A patent/NZ507639A/en unknown
- 1999-04-23 TR TR2001/02612T patent/TR200102612T2/xx unknown
- 1999-04-23 CA CA002329921A patent/CA2329921A1/en not_active Abandoned
- 1999-04-23 BR BRPI9909995-0A patent/BR9909995B1/pt not_active IP Right Cessation
- 1999-04-23 US US09/319,973 patent/US6313137B1/en not_active Expired - Fee Related
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- 1999-04-23 RU RU2000127020/04A patent/RU2235725C2/ru active
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2001
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Also Published As

Publication number	Publication date
HUP0102425A3 (en)	2002-12-28
EE04916B1 (et)	2007-10-15
HUP0102313A3 (en)	2002-10-28
EP1491542A3 (en)	2005-01-05
SK14922000A3 (sk)	2001-06-11
TR200102612T2 (tr)	2002-06-21
HUP0102313A2 (hu)	2001-12-28
BR9909995B1 (pt)	2010-07-13
IL139200A (en)	2010-04-29
EP1073656A1 (en)	2001-02-07
NZ507639A (en)	2004-01-30
NO20005450D0 (no)	2000-10-27
KR20010043134A (ko)	2001-05-25
MY121379A (en)	2006-01-28
CN1306533A (zh)	2001-08-01
ZA200005797B (en)	2002-01-18
JP3692034B2 (ja)	2005-09-07
SA99200064B1 (ar)	2006-10-11
ES2252975T3 (es)	2006-05-16
CZ293977B6 (cs)	2004-09-15
PL195000B1 (pl)	2007-07-31
IL139200A0 (en)	2001-11-25
AR015768A1 (es)	2001-05-16
JP3883383B2 (ja)	2007-02-21
MY121389A (en)	2006-01-28
RU2235725C2 (ru)	2004-09-10
NO20005451D0 (no)	2000-10-27
AU4300699A (en)	1999-11-16
TR200102728T2 (tr)	2002-06-21
BR9909996B1 (pt)	2010-08-24
KR100595806B1 (ko)	2006-07-03
SI1073656T1 (sl)	2006-02-28
WO1999055706A1 (en)	1999-11-04
DK1073657T3 (da)	2006-03-13
HK1036984A1 (en)	2002-01-25
DE69937076T2 (de)	2008-05-29
KR20010043133A (ko)	2001-05-25
ID27530A (id)	2001-04-12
CZ292567B6 (cs)	2003-10-15
WO1999055706A9 (en)	2000-03-16
SA99200065A (ar)	2005-12-03
ATE372340T1 (de)	2007-09-15
SK14912000A3 (sk)	2001-06-11
TWI250159B (en)	2006-03-01
CA2329921A1 (en)	1999-11-04
TR200003176T2 (tr)	2001-03-21
ZA200005796B (en)	2002-01-18
EE200000664A (et)	2002-04-15
EP1491542B1 (en)	2007-09-05
BR9909995A (pt)	2000-12-26
HK1071139A1 (en)	2005-07-08
EE04676B1 (et)	2006-08-15
TR200003149T2 (tr)	2001-03-21
ATE307130T1 (de)	2005-11-15
DE69927803D1 (de)	2006-03-02
AU769190B2 (en)	2004-01-22
ATE372339T1 (de)	2007-09-15
ATE312101T1 (de)	2005-12-15
IS5683A (is)	2000-10-25
DE69937077T2 (de)	2008-05-29
CN1307577A (zh)	2001-08-08
US6313136B1 (en)	2001-11-06
US6313137B1 (en)	2001-11-06
SE9801526D0 (sv)	1998-04-29
NO20005450L (no)	2000-12-22
AR015769A1 (es)	2001-05-16
UA67769C2 (uk)	2004-07-15
CA2329922C (en)	2006-04-11
PL343797A1 (en)	2001-09-10
EP1491543B1 (en)	2007-09-05
AU769108B2 (en)	2004-01-15
BR9909996A (pt)	2000-12-26
PL343801A1 (en)	2001-09-10
EE200000626A (et)	2002-04-15
CZ20003982A3 (cs)	2001-02-14
DE69937077D1 (de)	2007-10-18
NZ507638A (en)	2003-10-31
DK1073656T3 (da)	2006-01-16
ES2249913T3 (es)	2006-04-01
DE69937076D1 (de)	2007-10-18
NO20005451L (no)	2000-12-27
HK1033457A1 (en)	2001-08-31
IL139297A (en)	2007-06-03
JP2002513024A (ja)	2002-05-08
EP1073656B1 (en)	2005-10-19
IL139297A0 (en)	2001-11-25
KR100595805B1 (ko)	2006-07-03
ID26819A (id)	2001-02-15
JP2002513025A (ja)	2002-05-08
IS5684A (is)	2000-10-25
WO1999055705A1 (en)	1999-11-04
CN1174980C (zh)	2004-11-10
RU2238271C2 (ru)	2004-10-20
HK1036981A1 (en)	2002-01-25
EP1073657B1 (en)	2005-12-07
UA66846C2 (uk)	2004-06-15
HUP0102425A2 (hu)	2001-11-28
DE69927803T2 (de)	2006-07-06
SA99200065B1 (ar)	2006-11-07
CN1165535C (zh)	2004-09-08
AU4300799A (en)	1999-11-16
HK1033317A1 (en)	2001-08-24
CA2329922A1 (en)	1999-11-04
NO318203B1 (no)	2005-02-14
EP1491542A2 (en)	2004-12-29
KR100650472B1 (ko)	2006-11-28
KR20050121760A (ko)	2005-12-27
DE69928792T2 (de)	2006-07-20
DE69928792D1 (de)	2006-01-12
EP1073657A1 (en)	2001-02-07
CZ20003981A3 (cs)	2001-03-14
SK285768B6 (sk)	2007-07-06
EP1491543A1 (en)	2004-12-29
TW490466B (en)	2002-06-11

Publication	Publication Date	Title
NO317262B1 (no)	2004-09-27	Imidazopyridinderivater som inhiberer magesyresekresjon, farmasoytisk formulering som inneholder slike derivater, fremgangsmate for deres fremstilling, anvendelse derav, og mellomprodukter.
RU2193036C2 (ru)	2002-11-20	Производные имидазо[1,2-а]пиридина, способы их получения, фармацевтический препарат на их основе, способ ингибирования секреции желудочной кислоты, способ лечения желудочно-кишечных воспалительных заболеваний и способ лечения состояний, в которые вовлечено инфицирование h.pylori
NO315704B1 (no)	2003-10-13	Heterocykliske forbindelser for inhibering av mavesyresekresjon, farmasöytiske preparater inneholdende slike forbindelser, fremgangsmåter forderes fremstilling, og deres anvendelse
NO311672B1 (no)	2002-01-02	Nye forbindelser, farmasöytisk preparat inneholdende slike forbindelser, deres anvendelser, og fremgangsmåter for deresfremstilling
EP1105390B1 (en)	2003-06-04	Imidazo[1,2-a]pyridine derivatives for the treatment of gastrointestinal diseases
MXPA00010239A (en)	2001-07-31	Imidazo pyridine derivatives which inhibit gastric acid secretion
MXPA00010231A (en)	2002-05-09	Imidazo pyridine derivatives which inhibit gastric acid secretion

Legal Events

Date	Code	Title	Description
2004-11-22	ERR	Erratum	Free format text: IMIDAZOPYRIDINDERIVATER SOM INHIBERER MAGESYRESEKRESJON, FARMASOYTISK FORMULERING SOM INNEHOLDER SLIKE DERIVATER, FREMGANGSMATE FOR DERES FREMSTILLING, ANVENDELSE DERAV, OG MELLOMPRODUKTER
2010-11-29	MM1K	Lapsed by not paying the annual fees