NO317304B1 - Tetrahydropyridoetere - Google Patents

Tetrahydropyridoetere Download PDF

Info

Publication number: NO317304B1
Authority: NO; Norway
Prior art keywords: hydroxy; dimethyl; phenyl; methoxyethoxy; naphthyridine
Prior art date: 1998-09-23

Application number

NO20011243A

Other languages

English (en)

Norwegian (no)

Other versions

NO20011243L (no

NO20011243D0 (no

Inventor

Gerhard Grundler

Jorg Senn-Bilfinger

Stefan Postius

Wolfgang-Alexander Simon

Ernst Sturm

Guido Hanauer

Reinhard Huber

Wolfgang Kromer

Original Assignee

Altana Pharma Ag

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.)

1998-09-23

Filing date

2001-03-12

Publication date

2004-10-04

2001-03-12 Application filed by Altana Pharma Ag filed Critical Altana Pharma Ag

2001-03-12 Publication of NO20011243L publication Critical patent/NO20011243L/no

2001-03-12 Publication of NO20011243D0 publication Critical patent/NO20011243D0/no

2004-10-04 Publication of NO317304B1 publication Critical patent/NO317304B1/no

Links

150000001875 compounds Chemical class 0.000 claims abstract description 93
PWILYDZRJORZDR-MISYRCLQSA-N (7r,8r,9r)-7-(2-methoxyethoxy)-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OCCOC)=CC=CC=C1 PWILYDZRJORZDR-MISYRCLQSA-N 0.000 claims abstract 3
-1 hydroxy, methoxy, ethoxy, isopropoxy, methoxyethoxy Chemical group 0.000 claims description 48
150000003839 salts Chemical class 0.000 claims description 46
239000001257 hydrogen Substances 0.000 claims description 35
229910052739 hydrogen Inorganic materials 0.000 claims description 35
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
125000001424 substituent group Chemical group 0.000 claims description 28
239000003814 drug Substances 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
229940079593 drug Drugs 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
239000000546 pharmaceutical excipient Substances 0.000 claims description 9
238000011282 treatment Methods 0.000 claims description 9
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
208000018522 Gastrointestinal disease Diseases 0.000 claims description 2
229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
230000002265 prevention Effects 0.000 claims description 2
PFUDJBXGGYVENA-BHIYHBOVSA-N (7r,8r,9r)-7,8-dimethoxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine Chemical compound C1([C@@H]2[C@H]([C@@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OC)OC)=CC=CC=C1 PFUDJBXGGYVENA-BHIYHBOVSA-N 0.000 claims 1
RJASEHFHFJEXPR-BHIYHBOVSA-N (7r,8r,9r)-7-ethoxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OCC)=CC=CC=C1 RJASEHFHFJEXPR-BHIYHBOVSA-N 0.000 claims 1
GDQBYAHOQAFREY-RYQLBKOJSA-N (7r,8s,9s)-7-methoxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@H]2[C@H](O)[C@@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OC)=CC=CC=C1 GDQBYAHOQAFREY-RYQLBKOJSA-N 0.000 claims 1
LHJMQBVQSCNUMD-RLLQIKCJSA-N (7s,8r,9r)-2,3-dimethyl-9-phenyl-7-propan-2-yloxy-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OC(C)C)=CC=CC=C1 LHJMQBVQSCNUMD-RLLQIKCJSA-N 0.000 claims 1
RJASEHFHFJEXPR-QRQLOZEOSA-N (7s,8r,9r)-7-ethoxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OCC)=CC=CC=C1 RJASEHFHFJEXPR-QRQLOZEOSA-N 0.000 claims 1
GDQBYAHOQAFREY-NXHRZFHOSA-N (7s,8r,9r)-7-methoxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OC)=CC=CC=C1 GDQBYAHOQAFREY-NXHRZFHOSA-N 0.000 claims 1
GDQBYAHOQAFREY-SZMVWBNQSA-N (7s,8s,9s)-7-methoxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@H]2[C@H](O)[C@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OC)=CC=CC=C1 GDQBYAHOQAFREY-SZMVWBNQSA-N 0.000 claims 1
230000028327 secretion Effects 0.000 abstract description 2
210000004211 gastric acid Anatomy 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
238000000034 method Methods 0.000 description 25
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
238000002844 melting Methods 0.000 description 19
230000008018 melting Effects 0.000 description 19
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 16
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
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239000002904 solvent Substances 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
238000004128 high performance liquid chromatography Methods 0.000 description 10
239000012074 organic phase Substances 0.000 description 10
239000000741 silica gel Substances 0.000 description 10
229910002027 silica gel Inorganic materials 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 9
239000003480 eluent Substances 0.000 description 8
239000000203 mixture Substances 0.000 description 8
230000002496 gastric effect Effects 0.000 description 7
239000000047 product Substances 0.000 description 7
238000000746 purification Methods 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
FHHGNULEXOWEKU-DJIMGWMZSA-N (7r,8r,9r)-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine-7,8-diol Chemical compound C1([C@H]2NC=3C4=NC(=C(N4C=CC=3[C@@H](O)[C@@H]2O)C)C)=CC=CC=C1 FHHGNULEXOWEKU-DJIMGWMZSA-N 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
239000013078 crystal Substances 0.000 description 5
239000012153 distilled water Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000010413 mother solution Substances 0.000 description 5
239000007858 starting material Substances 0.000 description 5
MXBVNILGVJVVMH-UHFFFAOYSA-N 1,7-naphthyridine Chemical compound C1=NC=CC2=CC=CN=C21 MXBVNILGVJVVMH-UHFFFAOYSA-N 0.000 description 4
FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 4
VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
201000010099 disease Diseases 0.000 description 4
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239000002244 precipitate Substances 0.000 description 4
238000011321 prophylaxis Methods 0.000 description 4
239000007787 solid Substances 0.000 description 4
210000002784 stomach Anatomy 0.000 description 4
239000000725 suspension Substances 0.000 description 4
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 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
108010079943 Pentagastrin Proteins 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000003795 chemical substances by application 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
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 3
229960000444 pentagastrin Drugs 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 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
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
241000590002 Helicobacter pylori Species 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
208000008469 Peptic Ulcer Diseases 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
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230000009858 acid secretion Effects 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 description 2
239000012300 argon atmosphere Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
239000000812 cholinergic antagonist Substances 0.000 description 2
MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
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POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
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150000004677 hydrates Chemical class 0.000 description 2
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230000000968 intestinal effect Effects 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
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VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 2
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239000012279 sodium borohydride Substances 0.000 description 2
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229910000104 sodium hydride Inorganic materials 0.000 description 2
239000012453 solvate Substances 0.000 description 2
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
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FHHGNULEXOWEKU-HYVNUMGLSA-N (7s,8r,9r)-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine-7,8-diol Chemical compound C1([C@H]2NC=3C4=NC(=C(N4C=CC=3[C@H](O)[C@@H]2O)C)C)=CC=CC=C1 FHHGNULEXOWEKU-HYVNUMGLSA-N 0.000 description 1
HZARBZKYLFMYGP-RHSMWYFYSA-N (8r,9r)-8-hydroxy-2,3-dimethyl-9-phenyl-9,10-dihydro-8h-imidazo[1,2-h][1,7]naphthyridin-7-one Chemical compound C1([C@H]2NC=3C4=NC(=C(N4C=CC=3C(=O)[C@@H]2O)C)C)=CC=CC=C1 HZARBZKYLFMYGP-RHSMWYFYSA-N 0.000 description 1
HZARBZKYLFMYGP-YOEHRIQHSA-N (8s,9s)-8-hydroxy-2,3-dimethyl-9-phenyl-9,10-dihydro-8h-imidazo[1,2-h][1,7]naphthyridin-7-one Chemical compound C1([C@@H]2NC=3C4=NC(=C(N4C=CC=3C(=O)[C@H]2O)C)C)=CC=CC=C1 HZARBZKYLFMYGP-YOEHRIQHSA-N 0.000 description 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-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
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VSWPGAIWKHPTKX-UHFFFAOYSA-N 1-methyl-10-[2-(4-methyl-1-piperazinyl)-1-oxoethyl]-5H-thieno[3,4-b][1,5]benzodiazepin-4-one Chemical compound C1CN(C)CCN1CC(=O)N1C2=CC=CC=C2NC(=O)C2=CSC(C)=C21 VSWPGAIWKHPTKX-UHFFFAOYSA-N 0.000 description 1
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YGTUPRIZNBMOFV-UHFFFAOYSA-N 2-(4-hydroxybenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=C(O)C=C1 YGTUPRIZNBMOFV-UHFFFAOYSA-N 0.000 description 1
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BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
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SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 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
- C07D471/12—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 three hetero rings
- C07D471/14—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- 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

NO20011243A 1998-09-23 2001-03-12 Tetrahydropyridoetere NO317304B1 (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
EP98117988		1998-09-23
DE19843504		1998-09-23
PCT/EP1999/006899 WO2000017200A1 (en)	1998-09-23	1999-09-17	Tetrahydropyridoethers

Publications (3)

Publication Number	Publication Date
NO20011243L NO20011243L (no)	2001-03-12
NO20011243D0 NO20011243D0 (no)	2001-03-12
NO317304B1 true NO317304B1 (no)	2004-10-04

Family

ID=26049024

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20011243A NO317304B1 (no)	1998-09-23	2001-03-12	Tetrahydropyridoetere

Country Status (31)

Country	Link
US (4)	US6436953B1 (ja)
EP (1)	EP1115725B1 (ja)
JP (1)	JP4145492B2 (ja)
KR (1)	KR100668400B1 (ja)
CN (2)	CN100506821C (ja)
AT (1)	ATE231862T1 (ja)
AU (1)	AU763463B2 (ja)
BG (1)	BG65195B1 (ja)
BR (1)	BR9914044A (ja)
CA (1)	CA2344251A1 (ja)
CZ (1)	CZ292335B6 (ja)
DE (1)	DE69905178T2 (ja)
DK (1)	DK1115725T3 (ja)
EA (1)	EA005377B1 (ja)
EE (1)	EE04677B1 (ja)
ES (1)	ES2191464T3 (ja)
GE (1)	GEP20032926B (ja)
HK (1)	HK1038360B (ja)
HR (1)	HRP20010224A2 (ja)
HU (1)	HUP0102990A3 (ja)
ID (1)	ID28896A (ja)
IL (2)	IL142063A0 (ja)
NO (1)	NO317304B1 (ja)
NZ (1)	NZ510610A (ja)
PL (1)	PL193616B1 (ja)
PT (1)	PT1115725E (ja)
RS (1)	RS50145B (ja)
SI (1)	SI1115725T1 (ja)
SK (1)	SK285165B6 (ja)
TR (1)	TR200100805T2 (ja)
WO (1)	WO2000017200A1 (ja)

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1999
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Also Published As

Publication number	Publication date
HUP0102990A2 (hu)	2002-01-28
CA2344251A1 (en)	2000-03-30
DE69905178D1 (de)	2003-03-06
ID28896A (id)	2001-07-12
KR100668400B1 (ko)	2007-01-17
NZ510610A (en)	2003-07-25
CN1560055A (zh)	2005-01-05
RS50145B (sr)	2009-03-25
EE200100172A (et)	2002-06-17
CN1155598C (zh)	2004-06-30
ES2191464T3 (es)	2003-09-01
BG105270A (en)	2001-11-30
EA005377B1 (ru)	2005-02-24
BG65195B1 (bg)	2007-06-29
KR20010075223A (ko)	2001-08-09
HUP0102990A3 (en)	2002-09-30
SK285165B6 (sk)	2006-07-07
NO20011243L (no)	2001-03-12
US6436953B1 (en)	2002-08-20
CZ292335B6 (cs)	2003-09-17
ATE231862T1 (de)	2003-02-15
US20040162310A1 (en)	2004-08-19
JP2002526499A (ja)	2002-08-20
GEP20032926B (en)	2003-03-25
WO2000017200A1 (en)	2000-03-30
BR9914044A (pt)	2001-12-04
US6696460B2 (en)	2004-02-24
DE69905178T2 (de)	2003-07-17
AU763463B2 (en)	2003-07-24
PT1115725E (pt)	2003-06-30
EA200100315A1 (ru)	2001-10-22
AU6192099A (en)	2000-04-10
JP4145492B2 (ja)	2008-09-03
EE04677B1 (et)	2006-08-15
DK1115725T3 (da)	2003-06-23
SI1115725T1 (en)	2003-06-30
NO20011243D0 (no)	2001-03-12
HK1038360B (zh)	2003-05-16
US7393860B1 (en)	2008-07-01
EP1115725B1 (en)	2003-01-29
IL142063A (en)	2007-10-31
CN100506821C (zh)	2009-07-01
IL142063A0 (en)	2002-03-10
HRP20010224A2 (en)	2002-04-30
PL346617A1 (en)	2002-02-25
US20020169320A1 (en)	2002-11-14
HK1038360A1 (en)	2002-03-15
CZ20011082A3 (cs)	2001-09-12
EP1115725A1 (en)	2001-07-18
YU21401A (sh)	2004-03-12
CN1319101A (zh)	2001-10-24
US7105676B2 (en)	2006-09-12
PL193616B1 (pl)	2007-02-28
SK3992001A3 (en)	2001-12-03
TR200100805T2 (tr)	2001-08-21

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2010-04-26	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
US7393860B1 (en)	2008-07-01	Tetrahydropyridoethers
CA2156078C (en)	2005-02-01	New imidazopyridines
EP0971922B1 (en)	2004-04-28	Tetrahydropyrido compounds
EP1127059B1 (en)	2008-02-20	Imidazonaphthyridines
US6197783B1 (en)	2001-03-06	Tetrahydropyrido compounds
EP1286999B1 (en)	2007-12-19	PYRANO[2,3-c]IMIDAZO[1,2-a]PYRIDINE DERIVATIVES FOR THE TREATMENT OF GASTROINTESTINAL DISORDERS
AU700730B2 (en)	1999-01-14	Imidazopyridine-azolidinones
ZA200102107B (en)	2002-05-02	Tetrahydropyridoethers.
MXPA01003047A (en)	2003-11-07	Tetrahydropyridoethers