SK5072003A3 - Polysubstituted imidazopyridines as gastric secretion inhibitors - Google Patents

Polysubstituted imidazopyridines as gastric secretion inhibitors Download PDF

Info

Publication number: SK5072003A3
Authority: SK; Slovakia
Prior art keywords: alkoxy; alkyl; hydrogen; halogen; hydroxyl
Prior art date: 2000-10-25

Application number

SK507-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Jorg Senn-Bilfinger

Wilm Buhr

Wolfgang-Alexander Simon

Stefan Postius

Peter Zimmermann

Wolfgang Kromer

Bernhard Kohl

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.)

2000-10-25

Filing date

2001-10-23

Publication date

2003-09-11

2001-10-23 Application filed by Altana Pharma Ag filed Critical Altana Pharma Ag

2003-09-11 Publication of SK5072003A3 publication Critical patent/SK5072003A3/sk

Links

150000005232 imidazopyridines Chemical class 0.000 title abstract description 6
239000002731 stomach secretion inhibitor Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 237
125000001424 substituent group Chemical group 0.000 claims abstract description 96
239000001257 hydrogen Substances 0.000 claims description 680
229910052739 hydrogen Inorganic materials 0.000 claims description 680
-1 cyanomethyl Chemical group 0.000 claims description 399
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 363
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 278
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 247
229910052736 halogen Inorganic materials 0.000 claims description 211
150000002367 halogens Chemical class 0.000 claims description 208
229910052760 oxygen Inorganic materials 0.000 claims description 195
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 191
239000001301 oxygen Substances 0.000 claims description 191
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 147
150000003839 salts Chemical class 0.000 claims description 120
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 111
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 62
125000001544 thienyl group Chemical group 0.000 claims description 58
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 58
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 57
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 53
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 0.000 claims description 28
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 26
125000002541 furyl group Chemical group 0.000 claims description 26
125000003118 aryl group Chemical group 0.000 claims description 23
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 20
229910052757 nitrogen Inorganic materials 0.000 claims description 18
125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 claims description 17
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 17
125000002950 monocyclic group Chemical group 0.000 claims description 15
230000004962 physiological condition Effects 0.000 claims description 14
125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 13
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 13
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 13
125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 13
125000002883 imidazolyl group Chemical group 0.000 claims description 13
125000001041 indolyl group Chemical group 0.000 claims description 13
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 13
125000000842 isoxazolyl group Chemical group 0.000 claims description 13
125000001624 naphthyl group Chemical group 0.000 claims description 13
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
125000003226 pyrazolyl group Chemical group 0.000 claims description 13
125000004076 pyridyl group Chemical group 0.000 claims description 13
125000000714 pyrimidinyl group Chemical group 0.000 claims description 13
125000000168 pyrrolyl group Chemical group 0.000 claims description 13
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 13
125000000335 thiazolyl group Chemical group 0.000 claims description 13
229910052786 argon Inorganic materials 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 10
239000003814 drug Substances 0.000 claims description 9
101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
125000001153 fluoro group Chemical group F* 0.000 claims description 8
125000004043 oxo group Chemical group O=* 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
229910052701 rubidium Inorganic materials 0.000 claims description 8
239000000460 chlorine Chemical group 0.000 claims description 7
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
239000000546 pharmaceutical excipient Substances 0.000 claims description 6
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
230000002265 prevention Effects 0.000 claims description 5
125000004104 aryloxy group Chemical group 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
208000018522 Gastrointestinal disease Diseases 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 208
BQIKRTGTPBOIMK-UHFFFAOYSA-N [O]C[O] Chemical compound [O]C[O] BQIKRTGTPBOIMK-UHFFFAOYSA-N 0.000 claims 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
230000002496 gastric effect Effects 0.000 abstract description 8
230000002401 inhibitory effect Effects 0.000 abstract description 4
230000028327 secretion Effects 0.000 abstract description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 198
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 120
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 120
150000003254 radicals Chemical class 0.000 description 109
239000000243 solution Substances 0.000 description 82
239000000203 mixture Substances 0.000 description 67
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 51
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 43
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
238000006243 chemical reaction Methods 0.000 description 39
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 37
239000007787 solid Substances 0.000 description 37
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 33
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
229910052938 sodium sulfate Inorganic materials 0.000 description 30
235000011152 sodium sulphate Nutrition 0.000 description 30
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
239000011541 reaction mixture Substances 0.000 description 27
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
239000012044 organic layer Substances 0.000 description 26
239000000725 suspension Substances 0.000 description 25
239000012043 crude product Substances 0.000 description 24
239000012074 organic phase Substances 0.000 description 24
229920006395 saturated elastomer Polymers 0.000 description 24
239000012267 brine Substances 0.000 description 21
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 21
239000002904 solvent Substances 0.000 description 21
238000004440 column chromatography Methods 0.000 description 20
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
238000005160 1H NMR spectroscopy Methods 0.000 description 17
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 17
239000003480 eluent Substances 0.000 description 17
239000000741 silica gel Substances 0.000 description 17
229910002027 silica gel Inorganic materials 0.000 description 17
MXBVNILGVJVVMH-UHFFFAOYSA-N 1,7-naphthyridine Chemical compound C1=NC=CC2=CC=CN=C21 MXBVNILGVJVVMH-UHFFFAOYSA-N 0.000 description 15
238000002844 melting Methods 0.000 description 15
230000008018 melting Effects 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
238000000034 method Methods 0.000 description 14
235000019270 ammonium chloride Nutrition 0.000 description 13
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 11
238000002360 preparation method Methods 0.000 description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
239000000706 filtrate Substances 0.000 description 10
239000000047 product Substances 0.000 description 10
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
239000008346 aqueous phase Substances 0.000 description 9
229920001577 copolymer Chemical class 0.000 description 9
239000005457 ice water Substances 0.000 description 9
VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
238000010898 silica gel chromatography Methods 0.000 description 8
239000007858 starting material Substances 0.000 description 8
239000002253 acid Substances 0.000 description 7
229910052763 palladium Inorganic materials 0.000 description 7
230000009467 reduction Effects 0.000 description 7
235000017557 sodium bicarbonate Nutrition 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
239000012279 sodium borohydride Substances 0.000 description 7
229910000033 sodium borohydride Inorganic materials 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
230000000694 effects Effects 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 6
239000012071 phase Substances 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
239000002243 precursor Substances 0.000 description 6
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
210000002784 stomach Anatomy 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 5
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
235000011114 ammonium hydroxide Nutrition 0.000 description 5
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
238000006264 debenzylation reaction Methods 0.000 description 5
238000006266 etherification reaction Methods 0.000 description 5
238000005984 hydrogenation reaction Methods 0.000 description 5
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 4
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 4
SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
201000010099 disease Diseases 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
238000001914 filtration Methods 0.000 description 4
VQTUBCCKSQIDNK-UHFFFAOYSA-N iso-butene Natural products CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
AGGKIUHIZDLLQA-UHFFFAOYSA-N (2,3-dimethyl-8-phenylmethoxyimidazo[1,2-a]pyridin-6-yl)methanol Chemical compound C=1C(CO)=CN2C(C)=C(C)N=C2C=1OCC1=CC=CC=C1 AGGKIUHIZDLLQA-UHFFFAOYSA-N 0.000 description 3
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
RTDPHFVHMNFMFW-UHFFFAOYSA-N 1-(8-amino-2,3-dimethylimidazo[1,2-a]pyridin-7-yl)-3-thiophen-3-ylprop-2-en-1-one Chemical compound C1=CN2C(C)=C(C)N=C2C(N)=C1C(=O)C=CC=1C=CSC=1 RTDPHFVHMNFMFW-UHFFFAOYSA-N 0.000 description 3
ZPZCVEUCCXVENC-UHFFFAOYSA-N 1-(8-amino-2,3-dimethylimidazo[1,2-a]pyridin-7-yl)ethanone Chemical compound NC1=C(C(=O)C)C=CN2C(C)=C(C)N=C21 ZPZCVEUCCXVENC-UHFFFAOYSA-N 0.000 description 3
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
HLILKCXBVFGGPZ-YMPZKCBVSA-N [(7r,8r,9r)-10-acetyl-3-bromo-7-(2-methoxyethoxy)-2-methyl-9-phenyl-8,9-dihydro-7h-imidazo[1,2-h][1,7]naphthyridin-8-yl] 2,2-dimethylpropanoate Chemical compound C1([C@@H]2[C@@H](OC(=O)C(C)(C)C)[C@@H](C3=C(C4=NC(C)=C(Br)N4C=C3)N2C(C)=O)OCCOC)=CC=CC=C1 HLILKCXBVFGGPZ-YMPZKCBVSA-N 0.000 description 3
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
239000012346 acetyl chloride Substances 0.000 description 3
230000009858 acid secretion Effects 0.000 description 3
230000009471 action Effects 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
125000005196 alkyl carbonyloxy group Chemical group 0.000 description 3
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical group C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
238000010511 deprotection reaction Methods 0.000 description 3
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
125000004430 oxygen atom Chemical group O* 0.000 description 3
238000000746 purification Methods 0.000 description 3
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AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- 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
- 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

Landscapes

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

SK507-2003A 2000-10-25 2001-10-23 Polysubstituted imidazopyridines as gastric secretion inhibitors SK5072003A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP00123133		2000-10-25
PCT/EP2001/012207 WO2002034749A1 (en)	2000-10-25	2001-10-23	Polysubstituted imidazopyridines as gastric secretion inhibitors

Publications (1)

Publication Number	Publication Date
SK5072003A3 true SK5072003A3 (en)	2003-09-11

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Application Number	Title	Priority Date	Filing Date
SK507-2003A SK5072003A3 (en)	2000-10-25	2001-10-23	Polysubstituted imidazopyridines as gastric secretion inhibitors

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US (2)	US6869949B2 (ru)
EP (1)	EP1332143A1 (ru)
JP (1)	JP2004512338A (ru)
KR (1)	KR20040011423A (ru)
CN (1)	CN1692113A (ru)
AU (2)	AU2002210563B2 (ru)
BR (1)	BR0114873A (ru)
CA (1)	CA2426616A1 (ru)
EA (1)	EA008151B1 (ru)
HR (1)	HRP20030323A2 (ru)
HU (1)	HUP0302308A2 (ru)
IL (1)	IL154850A0 (ru)
MX (1)	MXPA03003706A (ru)
NO (1)	NO325736B1 (ru)
NZ (1)	NZ525281A (ru)
PL (1)	PL360412A1 (ru)
SK (1)	SK5072003A3 (ru)
WO (1)	WO2002034749A1 (ru)
ZA (1)	ZA200302038B (ru)

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DE10145457A1 (de)	2001-09-14	2003-04-03	Basf Ag	Substituierte Imidazo[1,2-a]-5,6,7,8-tetrahydropyridin-8-one, Verfahren zu ihrer Herstellung, sowie deren Verwendung zur Herstellung von Imidazo[1,2,-a]pyridinen
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HRP20050632A2 (hr) *	2002-12-20	2006-04-30	Altana Pharma Ag	Silil eteri
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.
AU2004226178A1 (en) *	2003-04-03	2004-10-14	Altana Pharma Ag	Process for the production of imidazopyridin-8-ones
AR044129A1 (es) *	2003-05-06	2005-08-24	Altana Pharma Ag	Compuestos intermedios de imidazopiridina. proceso de preparacion.
KR20060099524A (ko)	2003-11-03	2006-09-19	아스트라제네카 아베	무증상 위식도 역류의 치료를 위한 이미다조[1,2-ａ]피리딘유도체
AR046893A1 (es) *	2003-12-16	2005-12-28	Altana Pharma Ag	Bencimidazoles triciclicos
WO2005058894A1 (en)	2003-12-19	2005-06-30	Altana Pharma Ag	Intermediates for the preparation of tricyclic dihydropyrano -imidazo -pyridines derivatives
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2001
- 2001-10-23 EA EA200300478A patent/EA008151B1/ru not_active IP Right Cessation
- 2001-10-23 IL IL15485001A patent/IL154850A0/xx unknown
- 2001-10-23 JP JP2002537739A patent/JP2004512338A/ja active Pending
- 2001-10-23 MX MXPA03003706A patent/MXPA03003706A/es active IP Right Grant
- 2001-10-23 AU AU2002210563A patent/AU2002210563B2/en not_active Ceased
- 2001-10-23 WO PCT/EP2001/012207 patent/WO2002034749A1/en not_active Ceased
- 2001-10-23 CN CNA018177808A patent/CN1692113A/zh active Pending
- 2001-10-23 PL PL36041201A patent/PL360412A1/xx not_active Application Discontinuation
- 2001-10-23 SK SK507-2003A patent/SK5072003A3/sk not_active Application Discontinuation
- 2001-10-23 BR BR0114873-7A patent/BR0114873A/pt not_active IP Right Cessation
- 2001-10-23 AU AU1056302A patent/AU1056302A/xx active Pending
- 2001-10-23 EP EP01978447A patent/EP1332143A1/en not_active Withdrawn
- 2001-10-23 HR HR20030323A patent/HRP20030323A2/hr not_active Application Discontinuation
- 2001-10-23 KR KR10-2003-7005620A patent/KR20040011423A/ko not_active Ceased
- 2001-10-23 CA CA002426616A patent/CA2426616A1/en not_active Abandoned
- 2001-10-23 US US10/380,624 patent/US6869949B2/en not_active Expired - Fee Related
- 2001-10-23 NZ NZ525281A patent/NZ525281A/en unknown
- 2001-10-23 HU HU0302308A patent/HUP0302308A2/hu unknown
2003
- 2003-03-13 ZA ZA200302038A patent/ZA200302038B/en unknown
- 2003-04-24 NO NO20031830A patent/NO325736B1/no unknown
2004
- 2004-05-24 US US10/851,092 patent/US7141567B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
MXPA03003706A (es)	2005-01-25
ZA200302038B (en)	2004-04-22
EA200300478A1 (ru)	2003-12-25
AU1056302A (en)	2002-05-06
EP1332143A1 (en)	2003-08-06
HRP20030323A2 (hr)	2005-04-30
US20040106642A1 (en)	2004-06-03
US6869949B2 (en)	2005-03-22
US20040214852A1 (en)	2004-10-28
NO325736B1 (no)	2008-07-14
WO2002034749A1 (en)	2002-05-02
PL360412A1 (en)	2004-09-06
BR0114873A (pt)	2003-07-01
EA008151B1 (ru)	2007-04-27
US7141567B2 (en)	2006-11-28
NZ525281A (en)	2004-11-26
CA2426616A1 (en)	2002-05-02
IL154850A0 (en)	2003-10-31
CN1692113A (zh)	2005-11-02
AU2002210563B2 (en)	2007-03-01
HUP0302308A2 (hu)	2003-11-28
JP2004512338A (ja)	2004-04-22
NO20031830L (no)	2003-04-24
NO20031830D0 (no)	2003-04-24
KR20040011423A (ko)	2004-02-05

Legal Events

Date	Code	Title	Description
2010-10-07	FC9A	Refused patent application

Publication	Publication Date	Title
AU2002210563B2 (en)	2007-03-01	Polysubstituted imidazopyridines as gastric secretion inhibitors
AU2002210563A1 (en)	2002-07-11	Polysubstituted imidazopyridines as gastric secretion inhibitors
SK13872002A3 (sk)	2003-02-04	Alkylové imidazopyridínové deriváty, farmaceutický prostriedok s ich obsahom a ich použitie
CA2582294A1 (en)	2006-04-13	Condensed tricyclic benzimidazoles for the treatment of gastrointestinal disorders
US20060035892A1 (en)	2006-02-16	Nitrosated imidazopyridines
US20040235883A1 (en)	2004-11-25	Alkyl-substituted imidazopyridines for the treatment of gastrointestinal disorders
US20040235882A1 (en)	2004-11-25	Amino-substituted imidazopyridines for the treatment of gastrointestial diseases
EP1718648B1 (en)	2008-04-23	Tricyclic imidazopyridines and intermediates for the synthesis thereof
AU2002328995A1 (en)	2003-03-03	Alkyl-substituted imidazopyridines for the treatment of gastrointestinal disorders
US20070244173A1 (en)	2007-10-18	6,7-Dihydroxy-8-Phenyl-3,6,7,8-Tetrahydro-Chromeno [7,8-d] Imidazole Derivatives and Their Use as Gastric Acid Secretion Inhibitors
EP1797089A1 (en)	2007-06-20	Substituted tricyclic benzimidazoles