ZA200207635B - Pyrano[2,3-C]imidazo[-1,2-A]pyridine derivatives for the treatment of gastrointestinal disorders. - Google Patents

Pyrano[2,3-C]imidazo[-1,2-A]pyridine derivatives for the treatment of gastrointestinal disorders. Download PDF

Info

Publication number: ZA200207635B
Authority: ZA; South Africa
Prior art keywords: hydrogen; mmol; salts; hydroxy; acid
Prior art date: 2000-03-29

Application number

ZA200207635A

Other languages

English (en)

Inventor

Wolfgang-Alexander Simon

Stefan Postius

Wolfgang Kromer

Joerg Senn-Bilfinger

Wilm Buhr

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.)

2000-03-29

Filing date

2002-09-23

Publication date

2003-10-20

2002-09-23 Application filed by Altana Pharma Ag filed Critical Altana Pharma Ag

2003-10-20 Publication of ZA200207635B publication Critical patent/ZA200207635B/en

Links

238000011282 treatment Methods 0.000 title claims description 13
208000018522 Gastrointestinal disease Diseases 0.000 title claims description 4
150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 82
-1 hydroxy, methoxy, ethoxy, propoxy, isopropoxy, butoxy, methoxyethoxy Chemical group 0.000 claims description 42
150000003839 salts Chemical class 0.000 claims description 40
229910052739 hydrogen Inorganic materials 0.000 claims description 31
239000001257 hydrogen Substances 0.000 claims description 31
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
125000001424 substituent group Chemical group 0.000 claims description 21
239000003814 drug Substances 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
239000000546 pharmaceutical excipient Substances 0.000 claims description 4
230000002265 prevention Effects 0.000 claims description 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 76
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 58
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
239000000203 mixture Substances 0.000 description 29
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 28
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 24
229960004132 diethyl ether Drugs 0.000 description 22
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
239000000243 solution Substances 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
239000007787 solid Substances 0.000 description 19
238000002844 melting Methods 0.000 description 18
230000008018 melting Effects 0.000 description 18
239000012043 crude product Substances 0.000 description 16
VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical class C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 15
229920006395 saturated elastomer Polymers 0.000 description 14
229910052938 sodium sulfate Inorganic materials 0.000 description 14
235000011152 sodium sulphate Nutrition 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
239000002253 acid Substances 0.000 description 13
239000012267 brine Substances 0.000 description 13
238000004440 column chromatography Methods 0.000 description 13
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
239000000725 suspension Substances 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
239000012044 organic layer Substances 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
238000000034 method Methods 0.000 description 10
239000000047 product Substances 0.000 description 10
235000017557 sodium bicarbonate Nutrition 0.000 description 10
229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
230000003647 oxidation Effects 0.000 description 9
238000007254 oxidation reaction Methods 0.000 description 9
239000002904 solvent Substances 0.000 description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
230000002496 gastric effect Effects 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
201000010099 disease Diseases 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000011734 sodium Substances 0.000 description 5
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
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
230000010933 acylation Effects 0.000 description 4
238000005917 acylation reaction Methods 0.000 description 4
239000003638 chemical reducing agent Substances 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
238000010511 deprotection reaction Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000006266 etherification reaction Methods 0.000 description 4
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
238000011321 prophylaxis Methods 0.000 description 4
210000002784 stomach Anatomy 0.000 description 4
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
241000282414 Homo sapiens Species 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
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
235000019270 ammonium chloride Nutrition 0.000 description 3
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 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
150000002009 diols Chemical class 0.000 description 3
208000035475 disorder Diseases 0.000 description 3
230000027119 gastric acid secretion Effects 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
230000028327 secretion Effects 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000000126 substance Substances 0.000 description 3
UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 3
DMTADULPJIAIEO-UHFFFAOYSA-N 2,3-dimethyl-6,7-dihydro-5h-imidazo[1,2-a]pyridin-8-one Chemical compound O=C1CCCN2C(C)=C(C)N=C21 DMTADULPJIAIEO-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
229960000549 4-dimethylaminophenol Drugs 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
208000017189 Gastrointestinal inflammatory disease Diseases 0.000 description 2
241000590002 Helicobacter pylori Species 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
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108010079943 Pentagastrin Proteins 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
230000009858 acid secretion Effects 0.000 description 2
229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
125000001309 chloro group Chemical group Cl* 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
229960002626 clarithromycin Drugs 0.000 description 2
AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin 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)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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238000006735 epoxidation reaction Methods 0.000 description 2
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230000002401 inhibitory effect Effects 0.000 description 2
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230000000968 intestinal effect Effects 0.000 description 2
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ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
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PIKFXKSSNMLKLP-UHFFFAOYSA-N 1,2,3,5-tetrahydroimidazo[1,2-h][1,7]naphthyridine Chemical class C1C=C2C=CC=NC2=C2N1CCN2 PIKFXKSSNMLKLP-UHFFFAOYSA-N 0.000 description 1
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238000005160 1H NMR spectroscopy Methods 0.000 description 1
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BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
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125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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GKCBAIGFKIBETG-UHFFFAOYSA-N tetracaine Chemical compound CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 GKCBAIGFKIBETG-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—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

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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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

ZA200207635A 2000-03-29 2002-09-23 Pyrano[2,3-C]imidazo[-1,2-A]pyridine derivatives for the treatment of gastrointestinal disorders. ZA200207635B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP00106690		2000-03-29

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ZA200207635B true ZA200207635B (en)	2003-10-20

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Country	Link
US (2)	US20030100578A1 (de)
EP (1)	EP1286999B1 (de)
JP (1)	JP2003528877A (de)
KR (1)	KR20020082494A (de)
CN (1)	CN1221554C (de)
AT (1)	ATE381568T1 (de)
AU (1)	AU784611B2 (de)
BR (1)	BR0109589A (de)
CA (1)	CA2404466A1 (de)
CZ (1)	CZ20023210A3 (de)
DE (1)	DE60131968T2 (de)
EA (1)	EA006095B1 (de)
ES (1)	ES2298233T3 (de)
HR (1)	HRP20020855A2 (de)
HU (1)	HUP0300569A3 (de)
MX (1)	MXPA02009550A (de)
NO (1)	NO20024572L (de)
NZ (1)	NZ520836A (de)
PL (1)	PL365824A1 (de)
SK (1)	SK13862002A3 (de)
WO (1)	WO2001072755A1 (de)
ZA (1)	ZA200207635B (de)

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JP2003528876A (ja) *	2000-03-29	2003-09-30	アルタナファルマアクチエンゲゼルシャフト	アルキル化されたイミダゾピリジン誘導体
EA008151B1 (ru) *	2000-10-25	2007-04-27	Алтана Фарма Аг	Полизамещенные имидазопиридины в качестве ингибиторов желудочной секреции
AU2003288071A1 (en)	2002-11-19	2004-06-15	Altana Pharma Ag	8-substituted imidazopyridines
MXPA05008490A (es) *	2003-02-17	2005-10-18	Altana Pharma Ag	Combinaciones que contienen imidazopiridinas y su uso en el tratamiento de enfermedades gastrointestinales inflamatorias.
AR044129A1 (es) *	2003-05-06	2005-08-24	Altana Pharma Ag	Compuestos intermedios de imidazopiridina. proceso de preparacion.
WO2004105795A1 (en) *	2003-05-27	2004-12-09	Altana Pharma Ag	Pharmaceutical combinations of a proton pump inhibitor and a compound which modifies gastrointestinal motility
KR20060099524A (ko)	2003-11-03	2006-09-19	아스트라제네카 아베	무증상 위식도 역류의 치료를 위한 이미다조[1,2-ａ]피리딘유도체
WO2005058894A1 (en)	2003-12-19	2005-06-30	Altana Pharma Ag	Intermediates for the preparation of tricyclic dihydropyrano -imidazo -pyridines derivatives
AR048869A1 (es) *	2004-04-26	2006-06-07	Altana Pharma Ag	Bencimidazoles triciclicos
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2001
- 2001-03-28 AU AU56228/01A patent/AU784611B2/en not_active Ceased
- 2001-03-28 MX MXPA02009550A patent/MXPA02009550A/es active IP Right Grant
- 2001-03-28 EP EP01929463A patent/EP1286999B1/de not_active Expired - Lifetime
- 2001-03-28 DE DE60131968T patent/DE60131968T2/de not_active Expired - Fee Related
- 2001-03-28 CZ CZ20023210A patent/CZ20023210A3/cs unknown
- 2001-03-28 HU HU0300569A patent/HUP0300569A3/hu unknown
- 2001-03-28 HR HRP20020855 patent/HRP20020855A2/hr not_active Application Discontinuation
- 2001-03-28 PL PL01365824A patent/PL365824A1/xx unknown
- 2001-03-28 CN CNB01807166XA patent/CN1221554C/zh not_active Expired - Fee Related
- 2001-03-28 BR BR0109589-7A patent/BR0109589A/pt not_active Application Discontinuation
- 2001-03-28 JP JP2001570664A patent/JP2003528877A/ja not_active Withdrawn
- 2001-03-28 CA CA002404466A patent/CA2404466A1/en not_active Abandoned
- 2001-03-28 KR KR1020027012691A patent/KR20020082494A/ko not_active Abandoned
- 2001-03-28 AT AT01929463T patent/ATE381568T1/de not_active IP Right Cessation
- 2001-03-28 ES ES01929463T patent/ES2298233T3/es not_active Expired - Lifetime
- 2001-03-28 NZ NZ520836A patent/NZ520836A/en unknown
- 2001-03-28 US US10/182,620 patent/US20030100578A1/en not_active Abandoned
- 2001-03-28 EA EA200200883A patent/EA006095B1/ru not_active IP Right Cessation
- 2001-03-28 SK SK1386-2002A patent/SK13862002A3/sk unknown
- 2001-03-28 WO PCT/EP2001/003510 patent/WO2001072755A1/en not_active Ceased
2002
- 2002-09-23 ZA ZA200207635A patent/ZA200207635B/en unknown
- 2002-09-24 NO NO20024572A patent/NO20024572L/no not_active Application Discontinuation
2004
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Also Published As

Publication number	Publication date
CN1221554C (zh)	2005-10-05
US20030100578A1 (en)	2003-05-29
ATE381568T1 (de)	2008-01-15
EP1286999B1 (de)	2007-12-19
HUP0300569A3 (en)	2004-10-28
HUP0300569A2 (hu)	2003-07-28
WO2001072755A1 (en)	2001-10-04
CZ20023210A3 (cs)	2003-01-15
KR20020082494A (ko)	2002-10-31
NO20024572D0 (no)	2002-09-24
ES2298233T3 (es)	2008-05-16
NZ520836A (en)	2005-01-28
DE60131968T2 (de)	2008-12-11
DE60131968D1 (de)	2008-01-31
CN1419556A (zh)	2003-05-21
EA200200883A1 (ru)	2003-04-24
EA006095B1 (ru)	2005-08-25
BR0109589A (pt)	2003-02-04
US20040180920A1 (en)	2004-09-16
EP1286999A1 (de)	2003-03-05
HK1053838A1 (en)	2003-11-07
US6936623B2 (en)	2005-08-30
PL365824A1 (en)	2005-01-10
MXPA02009550A (es)	2004-05-14
HRP20020855A2 (en)	2004-12-31
NO20024572L (no)	2002-09-24
AU5622801A (en)	2001-10-08
AU784611B2 (en)	2006-05-11
JP2003528877A (ja)	2003-09-30
CA2404466A1 (en)	2001-10-04
SK13862002A3 (sk)	2003-03-04

Publication	Publication Date	Title
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US5665730A (en)	1997-09-09	Pharmaceutically useful imidazopyridines
WO1998042707A1 (en)	1998-10-01	Tetrahydropyrido compounds
WO1998054188A1 (en)	1998-12-03	Fused dihydropyrans
US7189736B2 (en)	2007-03-13	Prodrugs of imidazopyridine derivatives
US6197783B1 (en)	2001-03-06	Tetrahydropyrido compounds
EP1286999B1 (de)	2007-12-19	PYRANO[2,3-c]IMIDAZO[1,2-a]PYRIDIN-DERIVATE ZUR BEHANDLUNG VON GASTROINTESTINALEN ERKRANKUNGEN
US6696461B2 (en)	2004-02-24	Tricyclic imidazopyridines
HK1053838B (en)	2008-09-05	Pyrano(2,3,-c)imidazo(1,2-a)pyridine derivatives for the treatment of gastrointestinal disorders
ZA200102107B (en)	2002-05-02	Tetrahydropyridoethers.