SK13872002A3 - Alkylové imidazopyridínové deriváty, farmaceutický prostriedok s ich obsahom a ich použitie - Google Patents

Alkylové imidazopyridínové deriváty, farmaceutický prostriedok s ich obsahom a ich použitie Download PDF

Info

Publication number: SK13872002A3
Authority: SK; Slovakia
Prior art keywords: alkyl; hydrogen; alkoxy; radical; alkenyl
Prior art date: 2000-03-29

Application number

SK1387-2002A

Other languages

English (en)

Slovak (sk)

Inventor

J�rg SENN-BILFINGER

Wilm Buhr

Wolfgang-Alexander Simon

Stefan Postius

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.)

2000-03-29

Filing date

2001-03-28

Publication date

2003-02-04

2001-03-28 Application filed by Altana Pharma Ag filed Critical Altana Pharma Ag

2003-02-04 Publication of SK13872002A3 publication Critical patent/SK13872002A3/sk

Links

125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 0.000 title claims description 10
150000001875 compounds Chemical class 0.000 claims abstract description 121
238000011282 treatment Methods 0.000 claims abstract description 13
230000002265 prevention Effects 0.000 claims abstract description 6
208000018522 Gastrointestinal disease Diseases 0.000 claims abstract description 5
239000001257 hydrogen Substances 0.000 claims description 127
229910052739 hydrogen Inorganic materials 0.000 claims description 127
150000002431 hydrogen Chemical class 0.000 claims description 101
-1 pyrrolidino, piperidino Chemical group 0.000 claims description 101
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 49
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 41
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
150000003839 salts Chemical class 0.000 claims description 37
229910052736 halogen Inorganic materials 0.000 claims description 31
150000002367 halogens Chemical class 0.000 claims description 31
229910052760 oxygen Inorganic materials 0.000 claims description 30
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 29
239000001301 oxygen Substances 0.000 claims description 29
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
125000001424 substituent group Chemical group 0.000 claims description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
239000003814 drug Substances 0.000 claims description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
239000000546 pharmaceutical excipient Substances 0.000 claims description 5
230000004962 physiological condition Effects 0.000 claims description 5
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 5
CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 claims description 4
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 4
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
229910006069 SO3H Inorganic materials 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 108
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 60
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
150000003254 radicals Chemical class 0.000 description 48
239000000203 mixture Substances 0.000 description 31
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
239000000243 solution Substances 0.000 description 26
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
238000000034 method Methods 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
239000012074 organic phase Substances 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 15
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
239000003480 eluent Substances 0.000 description 13
239000002904 solvent Substances 0.000 description 13
239000007858 starting material Substances 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
239000002253 acid Substances 0.000 description 10
229920006395 saturated elastomer Polymers 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
238000002360 preparation method Methods 0.000 description 9
239000000047 product Substances 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
239000013078 crystal Substances 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 7
230000002496 gastric effect Effects 0.000 description 7
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 7
229910052763 palladium Inorganic materials 0.000 description 7
239000002243 precursor Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
239000007787 solid Substances 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
238000004440 column chromatography Methods 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
238000000926 separation method Methods 0.000 description 6
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
239000012043 crude product Substances 0.000 description 5
238000006264 debenzylation reaction Methods 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000011734 sodium Substances 0.000 description 5
MXBVNILGVJVVMH-UHFFFAOYSA-N 1,7-naphthyridine Chemical class C1=NC=CC2=CC=CN=C21 MXBVNILGVJVVMH-UHFFFAOYSA-N 0.000 description 4
KTOQRRDVVIDEAA-UHFFFAOYSA-N 2-methylpropane Chemical compound [CH2]C(C)C KTOQRRDVVIDEAA-UHFFFAOYSA-N 0.000 description 4
0 Cc1c(C)nc2[n]1CC(*)CC2=O Chemical compound Cc1c(C)nc2[n]1CC(*)CC2=O 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
241000700159 Rattus Species 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
239000003054 catalyst Substances 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
238000006266 etherification reaction Methods 0.000 description 4
235000019439 ethyl acetate Nutrition 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 4
VQTUBCCKSQIDNK-UHFFFAOYSA-N iso-butene Natural products CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 4
238000011321 prophylaxis Methods 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
239000012279 sodium borohydride Substances 0.000 description 4
229910000033 sodium borohydride Inorganic materials 0.000 description 4
239000000725 suspension Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 3
WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 3
IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 description 3
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
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 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
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 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
229920001577 copolymer Chemical class 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
229940079593 drug Drugs 0.000 description 3
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 3
XFZLCTUONFKKGV-UHFFFAOYSA-N ethyl 2,3-dimethyl-8-phenylmethoxyimidazo[1,2-a]pyridine-6-carboxylate Chemical compound C12=NC(C)=C(C)N2C=C(C(=O)OCC)C=C1OCC1=CC=CC=C1 XFZLCTUONFKKGV-UHFFFAOYSA-N 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
125000001153 fluoro group Chemical group F* 0.000 description 3
230000027119 gastric acid secretion Effects 0.000 description 3
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-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
125000006239 protecting group Chemical group 0.000 description 3
238000010898 silica gel chromatography Methods 0.000 description 3
210000002784 stomach Anatomy 0.000 description 3
239000003826 tablet Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
239000003039 volatile agent Substances 0.000 description 3
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 2
LEIIWODOEBDUMK-APWZRJJASA-N (8s,9r)-8-hydroxy-2,3,8-trimethyl-9-phenyl-9,10-dihydroimidazo[1,2-h][1,7]naphthyridin-7-one Chemical compound C1([C@H]2NC=3C4=NC(=C(N4C=CC=3C(=O)[C@]2(O)C)C)C)=CC=CC=C1 LEIIWODOEBDUMK-APWZRJJASA-N 0.000 description 2
HZARBZKYLFMYGP-PBHICJAKSA-N (8s,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-PBHICJAKSA-N 0.000 description 2
CRPTXKKKIGGDBX-UHFFFAOYSA-N (z)-but-2-ene Chemical compound [CH2]C=CC CRPTXKKKIGGDBX-UHFFFAOYSA-N 0.000 description 2
GJWHXWMUGWZNTO-UHFFFAOYSA-N 2,2-dimethylpropane Chemical compound [CH2]C(C)(C)C GJWHXWMUGWZNTO-UHFFFAOYSA-N 0.000 description 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
ULOIAOPTGWSNHU-UHFFFAOYSA-N 2-butyl radical Chemical compound C[CH]CC ULOIAOPTGWSNHU-UHFFFAOYSA-N 0.000 description 2
VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 2
YTVAVHFVWDJYTF-UHFFFAOYSA-N 6,8-dibromo-2,3-dimethylimidazo[1,2-a]pyridine Chemical compound BrC1=CC(Br)=CN2C(C)=C(C)N=C21 YTVAVHFVWDJYTF-UHFFFAOYSA-N 0.000 description 2
CVQJKRFLJGJENU-UHFFFAOYSA-N 6-bromo-2,3-dimethyl-8-phenylmethoxyimidazo[1,2-a]pyridine Chemical compound C=1C(Br)=CN2C(C)=C(C)N=C2C=1OCC1=CC=CC=C1 CVQJKRFLJGJENU-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-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
208000012895 Gastric disease Diseases 0.000 description 2
208000017189 Gastrointestinal inflammatory disease Diseases 0.000 description 2
241000590002 Helicobacter pylori Species 0.000 description 2
125000002066 L-histidyl group Chemical group [H]N1C([H])=NC(C([H])([H])[C@](C(=O)[*])([H])N([H])[H])=C1[H] 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-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
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
BKVIQODYSREJQH-UHFFFAOYSA-M [Br-].CC(C)=C[Mg+] Chemical compound [Br-].CC(C)=C[Mg+] BKVIQODYSREJQH-UHFFFAOYSA-M 0.000 description 2
BFKVXNPJXXJUGQ-UHFFFAOYSA-N [CH2]CCCC Chemical compound [CH2]CCCC BFKVXNPJXXJUGQ-UHFFFAOYSA-N 0.000 description 2
PQGAHNJECSVDEI-UHFFFAOYSA-N [CH2]CCCCC Chemical compound [CH2]CCCCC PQGAHNJECSVDEI-UHFFFAOYSA-N 0.000 description 2
AQMHNCQZLQUNJI-UHFFFAOYSA-N [CH2]CCCCCC Chemical compound [CH2]CCCCCC AQMHNCQZLQUNJI-UHFFFAOYSA-N 0.000 description 2
230000009858 acid secretion Effects 0.000 description 2
230000010933 acylation Effects 0.000 description 2
RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 2
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 2
235000019270 ammonium chloride Nutrition 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
150000007514 bases Chemical class 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
UHURJXXAXXMMLW-UHFFFAOYSA-N but-3-en-1-yl radical Chemical compound [CH2]CC=C UHURJXXAXXMMLW-UHFFFAOYSA-N 0.000 description 2
229910002091 carbon monoxide Inorganic materials 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
239000000812 cholinergic antagonist Substances 0.000 description 2
238000004587 chromatography analysis Methods 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
229940126214 compound 3 Drugs 0.000 description 2
229940125898 compound 5 Drugs 0.000 description 2
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
229940037467 helicobacter pylori Drugs 0.000 description 2
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FSHIFTSNGFKDHD-UHFFFAOYSA-N ethyl 2,3-dimethyl-8-oxo-6,7-dihydro-5h-imidazo[1,2-a]pyridine-6-carboxylate Chemical compound C1C(C(=O)OCC)CC(=O)C2=NC(C)=C(C)N21 FSHIFTSNGFKDHD-UHFFFAOYSA-N 0.000 description 1
KXTWAYJAWXMGGG-UHFFFAOYSA-N ethyl 8-hydroxy-2,3-dimethyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-6-carboxylate Chemical compound C1C(C(=O)OCC)CC(O)C2=NC(C)=C(C)N21 KXTWAYJAWXMGGG-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
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210000003191 femoral vein Anatomy 0.000 description 1
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235000013355 food flavoring agent Nutrition 0.000 description 1
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239000001530 fumaric acid Substances 0.000 description 1
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239000007789 gas Substances 0.000 description 1
210000004211 gastric acid Anatomy 0.000 description 1
239000003349 gelling agent Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
229950006191 gluconic acid Drugs 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229960002182 imipenem Drugs 0.000 description 1
GSOSVVULSKVSLQ-JJVRHELESA-N imipenem hydrate Chemical compound O.C1C(SCCNC=N)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 GSOSVVULSKVSLQ-JJVRHELESA-N 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
208000028774 intestinal disease Diseases 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
230000003902 lesion Effects 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
239000003589 local anesthetic agent Substances 0.000 description 1
229960005015 local anesthetics Drugs 0.000 description 1
239000003120 macrolide antibiotic agent Substances 0.000 description 1
229940041033 macrolides Drugs 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
244000005700 microbiome Species 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000004957 nitroimidazoles Chemical class 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
SBQLYHNEIUGQKH-UHFFFAOYSA-N omeprazole Chemical compound N1=C2[CH]C(OC)=CC=C2N=C1S(=O)CC1=NC=C(C)C(OC)=C1C SBQLYHNEIUGQKH-UHFFFAOYSA-N 0.000 description 1
229960000381 omeprazole Drugs 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 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
150000002960 penicillins Chemical class 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
208000011906 peptic ulcer disease Diseases 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000002831 pharmacologic agent Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
RMHMFHUVIITRHF-UHFFFAOYSA-N pirenzepine Chemical compound C1CN(C)CCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=CC=C21 RMHMFHUVIITRHF-UHFFFAOYSA-N 0.000 description 1
229960004633 pirenzepine Drugs 0.000 description 1
150000007519 polyprotic acids Polymers 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
DITHIFQMPPCBCU-UHFFFAOYSA-N propa-1,2-diene Chemical compound [CH]=C=C DITHIFQMPPCBCU-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000005855 radiation Effects 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
238000010992 reflux Methods 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
BZGIPVGCJGXQTA-UHFFFAOYSA-N s-[2-(diethylamino)ethyl] n,n-diphenylcarbamothioate Chemical compound C=1C=CC=CC=1N(C(=O)SCCN(CC)CC)C1=CC=CC=C1 BZGIPVGCJGXQTA-UHFFFAOYSA-N 0.000 description 1
230000003248 secreting effect Effects 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
230000002048 spasmolytic effect Effects 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
208000018556 stomach disease Diseases 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
229950004351 telenzepine Drugs 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
229960002372 tetracaine Drugs 0.000 description 1
GKCBAIGFKIBETG-UHFFFAOYSA-N tetracaine Chemical compound CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 GKCBAIGFKIBETG-UHFFFAOYSA-N 0.000 description 1
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 1
235000019364 tetracycline Nutrition 0.000 description 1
150000003522 tetracyclines Chemical class 0.000 description 1
229940040944 tetracyclines Drugs 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000004448 titration Methods 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1

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
- C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
- 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
- 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

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (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)

SK1387-2002A 2000-03-29 2001-03-28 Alkylové imidazopyridínové deriváty, farmaceutický prostriedok s ich obsahom a ich použitie SK13872002A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP00106696		2000-03-29
PCT/EP2001/003507 WO2001072754A1 (en)	2000-03-29	2001-03-28	Alkylated imidazopyridine derivatives

Publications (1)

Publication Number	Publication Date
SK13872002A3 true SK13872002A3 (sk)	2003-02-04

Family

ID=8168272

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1387-2002A SK13872002A3 (sk)	2000-03-29	2001-03-28	Alkylové imidazopyridínové deriváty, farmaceutický prostriedok s ich obsahom a ich použitie

Country Status (23)

Country	Link
US (1)	US6916825B2 (de)
EP (1)	EP1313739B1 (de)
JP (1)	JP2003528876A (de)
KR (1)	KR100823762B1 (de)
CN (1)	CN1213049C (de)
AT (1)	ATE332302T1 (de)
AU (1)	AU783764B2 (de)
BR (1)	BR0109542A (de)
CA (1)	CA2404460A1 (de)
CZ (1)	CZ20023116A3 (de)
DE (1)	DE60121345T2 (de)
EA (1)	EA005215B1 (de)
ES (1)	ES2267737T3 (de)
HR (1)	HRP20020853A2 (de)
HU (1)	HUP0300578A3 (de)
IL (1)	IL151201A0 (de)
MX (1)	MXPA02009552A (de)
NO (1)	NO20024597L (de)
NZ (1)	NZ520835A (de)
PL (1)	PL357811A1 (de)
SK (1)	SK13872002A3 (de)
WO (1)	WO2001072754A1 (de)
ZA (1)	ZA200207636B (de)

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KR100860627B1 (ko)	2000-03-29	2008-09-29	니코메드 게엠베하	이미다조피리딘 유도체의 프로드러그
CA2404466A1 (en) *	2000-03-29	2001-10-04	Altana Pharma Ag	Pyrano[2,3-c]imidazo[-1,2-a]pyridine derivatives for the treatment of gastrointestinal disorders
KR20040011423A (ko) *	2000-10-25	2004-02-05	알타나 파마 아게	위액 분비 억제제로서의 다중치환된 이미다조피리딘
EP1419156A1 (de) *	2001-08-03	2004-05-19	ALTANA Pharma AG	Alkyl-substituierte imidazopyridine für die behandlung gastrointestinaler erkrankungen
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
US7314935B2 (en)	2002-02-15	2008-01-01	Altana Pharma Ag	Tricyclic n-acyl compounds
KR20050086584A (ko)	2002-11-19	2005-08-30	알타나 파마 아게	8-치환 이미다조피리딘
CA2509882A1 (en) *	2002-12-20	2004-07-08	Altana Pharma Ag	Silyl ethers
PL377581A1 (pl) *	2003-02-17	2006-02-06	Altana Pharma Ag	Połączenia zawierające imidazopirydyny oraz ich zastosowanie do leczenia chorób zapalnych przewodu pokarmowego
AR044129A1 (es)	2003-05-06	2005-08-24	Altana Pharma Ag	Compuestos intermedios de imidazopiridina. proceso de preparacion.
WO2005041961A1 (en)	2003-11-03	2005-05-12	Astrazeneca Ab	Imidazo [1,2-a] pyridine derivatives for the treatment of silent gastro-esophageal reflux
US7326784B2 (en)	2003-12-19	2008-02-05	Altana Pharma Ag	Intermediates for the preparation of tricyclic dihydropyrano-imidazo-pyridines derivatives
US7215655B2 (en) *	2004-01-09	2007-05-08	Interdigital Technology Corporation	Transport format combination selection in a wireless transmit/receive unit
AR047605A1 (es) *	2004-02-17	2006-01-25	Altana Pharma Ag	Imidazopiridinas triciclicas e intermediarios en la sintesis de las mismas,sus procesos de preparacion,composiciones farmaceuticas que los contienen y usos.
CA2582256A1 (en) *	2004-10-01	2006-04-13	Altana Pharma Ag	Substituted tricyclic benzimidazoles
EP1934215A1 (de) *	2005-09-22	2008-06-25	Nycomed GmbH	Isotopensubstituierte imidazopyridinderivate zur behandlung von erkrankungen des magen-darm-trakts
WO2008058990A1 (en) *	2006-11-16	2008-05-22	Nycomed Gmbh	7,7-disubstituted pyrano-[2,3-c]-imidazo-[1,2-a]-pyridine derivatives and their use as gastric acid secretion inhibitors
KR101677126B1 (ko)	2008-05-20	2016-11-22	노이로제스엑스, 인코포레이티드	탄산염 프로드러그 및 그것의 사용 방법
JP5757864B2 (ja)	2008-05-20	2015-08-05	ニューロジェシックス，インコーポレイテッド	水溶性アセトアミノフェン類似体
AU2015357498B2 (en) *	2014-12-06	2019-09-12	Intra-Cellular Therapies, Inc.	Organic compounds

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Publication number	Priority date	Publication date	Assignee	Title
US4468400A (en)	1982-12-20	1984-08-28	Schering Corporation	Antiulcer tricyclic imidazo [1,2-a]pyridines
SE9401197D0 (sv)	1994-04-11	1994-04-11	Astra Ab	Active compounds
IL131407A0 (en) *	1997-03-24	2001-01-28	Byk Gulden Lomberg Chem Fab	Tetrahydropyrido compounds medicaments containing the same and the use thereof
AU736767B2 (en) *	1997-05-28	2001-08-02	Altana Pharma Ag	Fused dihydropyrans
HUP0001555A3 (en) *	1997-10-30	2001-01-29	Altana Pharma Ag	Tetrahydro-imidazo-naphthyridine derivatives, pharmaceutical compositions thereof and process for their preparation
CA2404466A1 (en) *	2000-03-29	2001-10-04	Altana Pharma Ag	Pyrano[2,3-c]imidazo[-1,2-a]pyridine derivatives for the treatment of gastrointestinal disorders
CN1221553C (zh) *	2000-03-29	2005-10-05	奥坦纳医药公司	三环咪唑并吡啶类化合物及药物组合物
KR100860627B1 (ko) *	2000-03-29	2008-09-29	니코메드 게엠베하	이미다조피리딘 유도체의 프로드러그

2001
- 2001-03-28 HR HR20020853A patent/HRP20020853A2/hr not_active Application Discontinuation
- 2001-03-28 SK SK1387-2002A patent/SK13872002A3/sk unknown
- 2001-03-28 BR BR0109542-0A patent/BR0109542A/pt not_active Application Discontinuation
- 2001-03-28 IL IL15120101A patent/IL151201A0/xx unknown
- 2001-03-28 WO PCT/EP2001/003507 patent/WO2001072754A1/en not_active Ceased
- 2001-03-28 PL PL01357811A patent/PL357811A1/xx not_active Application Discontinuation
- 2001-03-28 AU AU44225/01A patent/AU783764B2/en not_active Ceased
- 2001-03-28 HU HU0300578A patent/HUP0300578A3/hu unknown
- 2001-03-28 CZ CZ20023116A patent/CZ20023116A3/cs unknown
- 2001-03-28 AT AT01917121T patent/ATE332302T1/de not_active IP Right Cessation
- 2001-03-28 CA CA002404460A patent/CA2404460A1/en not_active Abandoned
- 2001-03-28 US US10/240,039 patent/US6916825B2/en not_active Expired - Fee Related
- 2001-03-28 ES ES01917121T patent/ES2267737T3/es not_active Expired - Lifetime
- 2001-03-28 NZ NZ520835A patent/NZ520835A/en unknown
- 2001-03-28 KR KR1020027012843A patent/KR100823762B1/ko not_active Expired - Fee Related
- 2001-03-28 EA EA200200876A patent/EA005215B1/ru not_active IP Right Cessation
- 2001-03-28 CN CNB018071619A patent/CN1213049C/zh not_active Expired - Fee Related
- 2001-03-28 JP JP2001570663A patent/JP2003528876A/ja not_active Withdrawn
- 2001-03-28 MX MXPA02009552A patent/MXPA02009552A/es active IP Right Grant
- 2001-03-28 EP EP01917121A patent/EP1313739B1/de not_active Expired - Lifetime
- 2001-03-28 DE DE60121345T patent/DE60121345T2/de not_active Expired - Fee Related
2002
- 2002-09-23 ZA ZA200207636A patent/ZA200207636B/xx unknown
- 2002-09-25 NO NO20024597A patent/NO20024597L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
IL151201A0 (en)	2003-04-10
WO2001072754A8 (en)	2003-02-13
WO2001072754A1 (en)	2001-10-04
EP1313739B1 (de)	2006-07-05
NZ520835A (en)	2004-05-28
EA005215B1 (ru)	2004-12-30
EP1313739A1 (de)	2003-05-28
DE60121345D1 (de)	2006-08-17
US20030158193A1 (en)	2003-08-21
KR20030015221A (ko)	2003-02-20
NO20024597D0 (no)	2002-09-25
HUP0300578A2 (hu)	2003-07-28
CN1213049C (zh)	2005-08-03
CA2404460A1 (en)	2001-10-04
ATE332302T1 (de)	2006-07-15
PL357811A1 (en)	2004-07-26
MXPA02009552A (es)	2004-05-14
DE60121345T2 (de)	2007-07-19
BR0109542A (pt)	2003-06-10
US6916825B2 (en)	2005-07-12
AU4422501A (en)	2001-10-08
NO20024597L (no)	2002-09-25
HRP20020853A2 (en)	2005-02-28
HUP0300578A3 (en)	2009-01-28
CZ20023116A3 (cs)	2003-01-15
EA200200876A1 (ru)	2003-04-24
HK1056173A1 (en)	2004-02-06
ZA200207636B (en)	2003-04-04
CN1422274A (zh)	2003-06-04
KR100823762B1 (ko)	2008-04-21
AU783764B2 (en)	2005-12-01
JP2003528876A (ja)	2003-09-30
WO2001072754A9 (en)	2004-05-06
ES2267737T3 (es)	2007-03-16

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EP0971922B1 (de)	2004-04-28	Tetrahydropyridoverbindungen
EP0984969B1 (de)	2008-07-09	Anellierte dihydropyrane
EP1313739B1 (de)	2006-07-05	Alkylierte imidazopyridinderivate
US7189736B2 (en)	2007-03-13	Prodrugs of imidazopyridine derivatives
AU740578B2 (en)	2001-11-08	Tetrahydropyrido compounds
SK5072003A3 (en)	2003-09-11	Polysubstituted imidazopyridines as gastric secretion inhibitors
EP1303519B1 (de)	2007-03-07	Tricyclische imidazopyridine
HK1056173B (en)	2007-01-12	Alkylated imidazopyridine derivatives
AU2005293576A1 (en)	2006-04-20	Difluoro-substituted imidazopyridines
HK1056175B (en)	2006-05-04	Prodrugs of imidazopyridine derivatives
MXPA99010900A (en)	2000-09-04	Fused dihydropyrans
HRP980147A2 (en)	1999-02-28	Tetrahydropyrido compounds