EA007683B1 - Трициклические имидазопиридины - Google Patents
Трициклические имидазопиридины Download PDFInfo
- Publication number
- EA007683B1 EA007683B1 EA200400254A EA200400254A EA007683B1 EA 007683 B1 EA007683 B1 EA 007683B1 EA 200400254 A EA200400254 A EA 200400254A EA 200400254 A EA200400254 A EA 200400254A EA 007683 B1 EA007683 B1 EA 007683B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- alkyl
- denotes
- alkoxy
- hydrogen atom
- alkoxycarbonyl
- Prior art date
Links
- -1 cyanomethyl Chemical group 0.000 claims abstract description 214
- 150000001875 compounds Chemical class 0.000 claims abstract description 84
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 51
- 150000003839 salts Chemical class 0.000 claims abstract description 31
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract description 21
- 125000005843 halogen group Chemical group 0.000 claims abstract description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 10
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims abstract description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 6
- 125000002950 monocyclic group Chemical class 0.000 claims abstract description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 5
- 125000001041 indolyl group Chemical group 0.000 claims abstract description 4
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims abstract description 3
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims abstract description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 3
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims abstract description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims abstract description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims abstract description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 5
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 2
- YDZNRNHKJQTGCG-UHFFFAOYSA-N 1,1'-binaphthyl-2,2'-dicarboxylic acid Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=CC=C3C(=O)O)=C(C(O)=O)C=CC2=C1 YDZNRNHKJQTGCG-UHFFFAOYSA-N 0.000 claims 1
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 claims 1
- BMVNFJCUHHTZQU-UHFFFAOYSA-N 4,5,6,7-tetrabromo-1,3-dihydrobenzimidazol-2-one Chemical compound BrC1=C(Br)C(Br)=C2NC(O)=NC2=C1Br BMVNFJCUHHTZQU-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 230000028327 secretion Effects 0.000 abstract description 5
- 125000002541 furyl group Chemical group 0.000 abstract description 4
- 210000004051 gastric juice Anatomy 0.000 abstract description 4
- 229910052799 carbon Inorganic materials 0.000 abstract description 2
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 105
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 15
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 14
- 239000004202 carbamide Substances 0.000 description 14
- 235000013877 carbamide Nutrition 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 150000003254 radicals Chemical class 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000005160 1H NMR spectroscopy Methods 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 230000002829 reductive effect Effects 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 239000012047 saturated solution Substances 0.000 description 8
- 235000019270 ammonium chloride Nutrition 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 238000003818 flash chromatography Methods 0.000 description 7
- 239000006260 foam Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 125000004430 oxygen atom Chemical group O* 0.000 description 7
- 210000002784 stomach Anatomy 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- ONOJJCTXSDBVSP-UHFFFAOYSA-N imidazo[1,2-a]pyridine-6-carboxylic acid Chemical compound C1=C(C(=O)O)C=CC2=NC=CN21 ONOJJCTXSDBVSP-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 4
- 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 4
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- UVJHQYIOXKWHFD-UHFFFAOYSA-N cyclohexa-1,4-diene Chemical compound C1C=CCC=C1 UVJHQYIOXKWHFD-UHFFFAOYSA-N 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 125000006656 (C2-C4) alkenyl group Chemical group 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
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 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
- 241000700159 Rattus Species 0.000 description 3
- 230000009858 acid secretion Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000000812 cholinergic antagonist 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
- 238000004440 column chromatography Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- PWWXIULQEXRUCV-UHFFFAOYSA-N imidazo[1,2-a]pyridine-6-carboxamide Chemical compound C1=C(C(=O)N)C=CC2=NC=CN21 PWWXIULQEXRUCV-UHFFFAOYSA-N 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 229910052763 palladium Inorganic materials 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
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 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
- 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 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 230000006315 carbonylation Effects 0.000 description 2
- 238000005810 carbonylation reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 238000001212 derivatisation Methods 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- VVDUZZGYBOWDSQ-UHFFFAOYSA-M eschenmoser's salt Chemical compound [I-].C[N+](C)=C VVDUZZGYBOWDSQ-UHFFFAOYSA-M 0.000 description 2
- FBFFNWKKNHPMPI-UHFFFAOYSA-N ethyl 8-hydroxy-2,3-dimethyl-7-(3-oxo-3-phenylpropyl)imidazo[1,2-a]pyridine-6-carboxylate Chemical compound CCOC(=O)C1=CN2C(C)=C(C)N=C2C(O)=C1CCC(=O)C1=CC=CC=C1 FBFFNWKKNHPMPI-UHFFFAOYSA-N 0.000 description 2
- XTIYKXYLASGUCR-UHFFFAOYSA-N ethyl 8-hydroxy-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylate Chemical compound C1=C(C(=O)OCC)C=C(O)C2=NC(C)=C(C)N21 XTIYKXYLASGUCR-UHFFFAOYSA-N 0.000 description 2
- CYPSYBVTXYVDIS-UHFFFAOYSA-N ethyl 8-hydroxy-7-(3-hydroxy-3-phenylpropyl)-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylate Chemical compound CCOC(=O)C1=CN2C(C)=C(C)N=C2C(O)=C1CCC(O)C1=CC=CC=C1 CYPSYBVTXYVDIS-UHFFFAOYSA-N 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 210000000936 intestine Anatomy 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- SBMSLRMNBSMKQC-UHFFFAOYSA-N pyrrolidin-1-amine Chemical compound NN1CCCC1 SBMSLRMNBSMKQC-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 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
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 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
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01119321 | 2001-08-10 | ||
| PCT/EP2002/008505 WO2003014123A1 (en) | 2001-08-10 | 2002-07-31 | Tricyclic imidazopyridines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200400254A1 EA200400254A1 (ru) | 2004-08-26 |
| EA007683B1 true EA007683B1 (ru) | 2006-12-29 |
Family
ID=8178292
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200400254A EA007683B1 (ru) | 2001-08-10 | 2002-07-31 | Трициклические имидазопиридины |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US7223771B2 (https=) |
| EP (1) | EP1419163B9 (https=) |
| JP (1) | JP2005504761A (https=) |
| KR (1) | KR20040023739A (https=) |
| CN (1) | CN1329395C (https=) |
| AT (1) | ATE297931T1 (https=) |
| BR (1) | BR0211826A (https=) |
| CA (1) | CA2452803A1 (https=) |
| DE (1) | DE60204701T2 (https=) |
| DK (1) | DK1419163T5 (https=) |
| EA (1) | EA007683B1 (https=) |
| ES (1) | ES2243788T3 (https=) |
| HR (1) | HRP20040229A2 (https=) |
| HU (1) | HUP0500330A3 (https=) |
| IL (1) | IL159554A0 (https=) |
| MX (1) | MXPA04001277A (https=) |
| NO (1) | NO20040604L (https=) |
| NZ (1) | NZ531520A (https=) |
| PL (1) | PL368195A1 (https=) |
| PT (1) | PT1419163E (https=) |
| SI (1) | SI1419163T1 (https=) |
| TW (1) | TWD111798S1 (https=) |
| WO (1) | WO2003014123A1 (https=) |
| ZA (1) | ZA200400918B (https=) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100393720C (zh) | 2003-04-04 | 2008-06-11 | 奥坦纳医药公司 | 环苯并咪唑化合物 |
| AR044129A1 (es) | 2003-05-06 | 2005-08-24 | Altana Pharma Ag | Compuestos intermedios de imidazopiridina. proceso de preparacion. |
| JP2006528231A (ja) * | 2003-05-27 | 2006-12-14 | アルタナ ファルマ アクチエンゲゼルシャフト | プロトンポンプ阻害剤と胃腸運動性を変更する化合物との医薬品組合せ物 |
| EP1697358A1 (en) * | 2003-12-19 | 2006-09-06 | Altana Pharma AG | Intermediates for the preparation of tricyclic dihydropyrano -imidazo -pyridines derivatives |
| AR046941A1 (es) * | 2003-12-19 | 2006-01-04 | Altana Pharma Ag | Imidazopiridinas triciclicas y su uso como inhibidores de secrecion de acido gastrico |
| NZ549011A (en) * | 2004-02-17 | 2009-04-30 | Altana Pharma Ag | Tricyclic imidazopyridines and intermediates for the synthesis thereof |
| US20070191334A1 (en) * | 2004-03-17 | 2007-08-16 | Altana Pharma Ag | Tricyclic imidazopyridines |
| AU2005223397A1 (en) * | 2004-03-22 | 2005-09-29 | Altana Pharma Ag | 7, 8, 9, 10- tetrahydro-imidazo [2,1-a] isoquinoline derivatives and their use as gastric acid secretion inhibitors |
| AR048869A1 (es) * | 2004-04-26 | 2006-06-07 | Altana Pharma Ag | Bencimidazoles triciclicos |
| DE602005002751T2 (de) * | 2004-06-09 | 2008-07-17 | Nycomed Gmbh | Substituierte tricyclische benzimidazole |
| AR051041A1 (es) * | 2004-10-04 | 2006-12-13 | Altana Pharma Ag | Bencimidazoles triciclicos condensados |
| AR054772A1 (es) * | 2005-06-16 | 2007-07-18 | Altana Pharma Ag | Espiro- imidazopiridinas como inhibidores de la secrecion de acido gastrico |
| JP2009531390A (ja) * | 2006-03-31 | 2009-09-03 | ノバルティス アクチエンゲゼルシャフト | 有機化合物 |
| WO2008071766A2 (en) * | 2006-12-14 | 2008-06-19 | Nycomed Gmbh | Spiro-indene substituted imidazonaphythyridine and pyranoimidazopyridine derivatives as inhibitors of gastric acid secretion |
| KR200452179Y1 (ko) * | 2009-05-20 | 2011-02-10 | 주식회사 신성일렉스 | 항공 장애물 표시 장치 |
| EP2452680B1 (en) | 2009-07-09 | 2019-12-18 | RaQualia Pharma Inc. | Acid pump antagonist for the treatment of diseases involved in abnormal gastrointestinal motility |
| GB201321730D0 (en) | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic agents |
| KR20250136992A (ko) * | 2024-03-07 | 2025-09-17 | 대원제약주식회사 | 삼환식 유도체 및 이를 포함하는 약학적 조성물 |
Citations (4)
| 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 |
| WO1995027714A1 (en) * | 1994-04-11 | 1995-10-19 | Astra Aktiebolag | Active compounds |
| WO1998042707A1 (en) * | 1997-03-24 | 1998-10-01 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Tetrahydropyrido compounds |
| WO1998054188A1 (en) * | 1997-05-28 | 1998-12-03 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Fused dihydropyrans |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU740578B2 (en) * | 1997-03-24 | 2001-11-08 | Altana Pharma Ag | Tetrahydropyrido compounds |
| MXPA02009549A (es) * | 2000-03-29 | 2004-05-14 | Altana Pharma Ag | Imidazopiridinas triciclicas. |
-
2002
- 2002-07-31 MX MXPA04001277A patent/MXPA04001277A/es active IP Right Grant
- 2002-07-31 EA EA200400254A patent/EA007683B1/ru not_active IP Right Cessation
- 2002-07-31 PT PT02794528T patent/PT1419163E/pt unknown
- 2002-07-31 SI SI200230179T patent/SI1419163T1/sl unknown
- 2002-07-31 ES ES02794528T patent/ES2243788T3/es not_active Expired - Lifetime
- 2002-07-31 DE DE60204701T patent/DE60204701T2/de not_active Expired - Fee Related
- 2002-07-31 NZ NZ531520A patent/NZ531520A/en unknown
- 2002-07-31 WO PCT/EP2002/008505 patent/WO2003014123A1/en not_active Ceased
- 2002-07-31 HR HR20040229A patent/HRP20040229A2/hr not_active Application Discontinuation
- 2002-07-31 US US10/485,515 patent/US7223771B2/en not_active Expired - Fee Related
- 2002-07-31 BR BR0211826-2A patent/BR0211826A/pt not_active IP Right Cessation
- 2002-07-31 EP EP02794528A patent/EP1419163B9/en not_active Expired - Lifetime
- 2002-07-31 IL IL15955402A patent/IL159554A0/xx unknown
- 2002-07-31 PL PL02368195A patent/PL368195A1/xx not_active Application Discontinuation
- 2002-07-31 KR KR10-2004-7001988A patent/KR20040023739A/ko not_active Ceased
- 2002-07-31 HU HU0500330A patent/HUP0500330A3/hu unknown
- 2002-07-31 AT AT02794528T patent/ATE297931T1/de not_active IP Right Cessation
- 2002-07-31 CA CA002452803A patent/CA2452803A1/en not_active Abandoned
- 2002-07-31 DK DK02794528T patent/DK1419163T5/da active
- 2002-07-31 JP JP2003519072A patent/JP2005504761A/ja not_active Withdrawn
- 2002-07-31 CN CNB028156013A patent/CN1329395C/zh not_active Expired - Fee Related
-
2004
- 2004-02-04 ZA ZA200400918A patent/ZA200400918B/en unknown
- 2004-02-10 NO NO20040604A patent/NO20040604L/no not_active Application Discontinuation
-
2005
- 2005-04-21 TW TW094302316F patent/TWD111798S1/zh unknown
Patent Citations (4)
| 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 |
| WO1995027714A1 (en) * | 1994-04-11 | 1995-10-19 | Astra Aktiebolag | Active compounds |
| WO1998042707A1 (en) * | 1997-03-24 | 1998-10-01 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Tetrahydropyrido compounds |
| WO1998054188A1 (en) * | 1997-05-28 | 1998-12-03 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Fused dihydropyrans |
Non-Patent Citations (2)
| Title |
|---|
| KAMINSKI J.J. ET AL.: "Antiulcer Agents. 4. Conformational Considerations and the Antiulcer Activity of Substituted Imidazo'1,2-a!pyridines and Related Analogues", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, US. vol. 32, no. 8, 1989, pages 1686-1700, XP002160711, ISSN: 0022-2623, abstract, page 1693, left-hand column -page 1693, right-hand column * |
| KAMINSKI J.J. ET AL.: "ANTIULCER AGENTS. 5. INHIBITION OF GASTRIC H+/K+-ATPASE BY SUBSITUTED IMIDAZOL 1,2-A PYRIDINES AND RELATED ANALOGUES AND ITS IMPLICATION IN MODELING THE HIGH AFFINITY POTASSIUM ION BINDING SITE OF THE GASTRIC PROTON PUMP ENZYME", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, US, vol. 34, 1991, pages 533-541, XP000919185, ISSN: 0022-2623, page 540, left-hand column -page 541, left-hand column; example 4 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1541219A (zh) | 2004-10-27 |
| HUP0500330A3 (en) | 2009-12-28 |
| TWD111798S1 (zh) | 2006-07-11 |
| JP2005504761A (ja) | 2005-02-17 |
| PT1419163E (pt) | 2005-10-31 |
| DE60204701D1 (de) | 2005-07-21 |
| EP1419163B9 (en) | 2005-11-09 |
| ES2243788T3 (es) | 2005-12-01 |
| KR20040023739A (ko) | 2004-03-18 |
| DK1419163T3 (da) | 2005-10-17 |
| NO20040604L (no) | 2004-02-10 |
| DK1419163T5 (da) | 2005-12-19 |
| ZA200400918B (en) | 2005-04-20 |
| HUP0500330A2 (hu) | 2005-07-28 |
| US7223771B2 (en) | 2007-05-29 |
| EP1419163B1 (en) | 2005-06-15 |
| BR0211826A (pt) | 2005-06-28 |
| PL368195A1 (en) | 2005-03-21 |
| WO2003014123A1 (en) | 2003-02-20 |
| ATE297931T1 (de) | 2005-07-15 |
| EP1419163A1 (en) | 2004-05-19 |
| CN1329395C (zh) | 2007-08-01 |
| MXPA04001277A (es) | 2004-05-27 |
| IL159554A0 (en) | 2004-06-01 |
| DE60204701T2 (de) | 2006-08-03 |
| SI1419163T1 (sl) | 2005-12-31 |
| HK1066213A1 (en) | 2005-03-18 |
| HRP20040229A2 (en) | 2005-02-28 |
| NZ531520A (en) | 2005-10-28 |
| CA2452803A1 (en) | 2003-02-20 |
| EA200400254A1 (ru) | 2004-08-26 |
| US20050049272A1 (en) | 2005-03-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): BY RU |