ZA200005796B - Imidazo pyridine derivatives which inhibit gastric acid secretion. - Google Patents
Imidazo pyridine derivatives which inhibit gastric acid secretion. Download PDFInfo
- Publication number
- ZA200005796B ZA200005796B ZA200005796A ZA200005796A ZA200005796B ZA 200005796 B ZA200005796 B ZA 200005796B ZA 200005796 A ZA200005796 A ZA 200005796A ZA 200005796 A ZA200005796 A ZA 200005796A ZA 200005796 B ZA200005796 B ZA 200005796B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- compound
- formula
- alkoxy
- ethyl
- Prior art date
Links
- 230000027119 gastric acid secretion Effects 0.000 title claims description 10
- 125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 140
- 150000001875 compounds Chemical class 0.000 claims description 115
- -1 imidazotyl Chemical group 0.000 claims description 31
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 150000002367 halogens Chemical class 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 20
- 238000011282 treatment Methods 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 16
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 15
- 125000004076 pyridyl group Chemical group 0.000 claims description 15
- 125000001624 naphthyl group Chemical group 0.000 claims description 14
- 125000002883 imidazolyl group Chemical group 0.000 claims description 13
- 125000001041 indolyl group Chemical group 0.000 claims description 13
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 12
- 239000012442 inert solvent Substances 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 11
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 10
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 208000017189 Gastrointestinal inflammatory disease Diseases 0.000 claims description 9
- 241000282414 Homo sapiens Species 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 9
- 125000002541 furyl group Chemical group 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 8
- 125000004185 ester group Chemical group 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 238000011321 prophylaxis Methods 0.000 claims description 6
- 241000590002 Helicobacter pylori Species 0.000 claims description 5
- 239000004599 antimicrobial Substances 0.000 claims description 5
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 238000009472 formulation Methods 0.000 claims description 5
- 210000001156 gastric mucosa Anatomy 0.000 claims description 5
- 229940037467 helicobacter pylori Drugs 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 208000015181 infectious disease Diseases 0.000 claims description 5
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 230000005764 inhibitory process Effects 0.000 claims description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- ZYIBSYLOZXPIFU-QFIPXVFZSA-N (2s)-1-[8-[(2-ethyl-6-methylphenyl)methylamino]-2,3-dimethylimidazo[1,2-a]pyridine-6-carbonyl]pyrrolidine-2-carboxamide Chemical compound CCC1=CC=CC(C)=C1CNC1=CC(C(=O)N2[C@@H](CCC2)C(N)=O)=CN2C1=NC(C)=C2C ZYIBSYLOZXPIFU-QFIPXVFZSA-N 0.000 claims description 2
- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 2
- AFXWDWGDRAFKLH-UHFFFAOYSA-N n-(4-ethoxyphenyl)-8-[(2-ethyl-6-methylphenyl)methylamino]-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound C1=CC(OCC)=CC=C1NC(=O)C1=CN2C(C)=C(C)N=C2C(NCC=2C(=CC=CC=2C)CC)=C1 AFXWDWGDRAFKLH-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 11
- 230000002401 inhibitory effect Effects 0.000 claims 3
- 241000282412 Homo Species 0.000 claims 2
- FGSCZMLSHATKFV-UHFFFAOYSA-N [8-[(2-ethyl-6-methylphenyl)methylamino]-2,3-dimethylimidazo[1,2-a]pyridin-6-yl]-morpholin-4-ylmethanone Chemical compound CCC1=CC=CC(C)=C1CNC1=CC(C(=O)N2CCOCC2)=CN2C1=NC(C)=C2C FGSCZMLSHATKFV-UHFFFAOYSA-N 0.000 claims 1
- 230000000845 anti-microbial effect Effects 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims 1
- 229940126409 proton pump inhibitor Drugs 0.000 claims 1
- 239000000612 proton pump inhibitor Substances 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 4
- 239000012317 TBTU Substances 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 239000007903 gelatin capsule Substances 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- HVOLVUZPFZNVPE-UHFFFAOYSA-N 8-[(2-ethyl-6-methylphenyl)methylamino]-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylic acid Chemical compound CCC1=CC=CC(C)=C1CNC1=CC(C(O)=O)=CN2C1=NC(C)=C2C HVOLVUZPFZNVPE-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 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
- 239000012458 free base Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000651 prodrug Substances 0.000 description 3
- 229940002612 prodrug Drugs 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- 229920000945 Amylopectin Polymers 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- 241000792859 Enema Species 0.000 description 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 239000004098 Tetracycline Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229960003022 amoxicillin Drugs 0.000 description 2
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 2
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 235000013681 dietary sucrose Nutrition 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000007920 enema Substances 0.000 description 2
- 229940095399 enema Drugs 0.000 description 2
- 229940093499 ethyl acetate Drugs 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 201000000052 gastrinoma Diseases 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 description 2
- 150000005232 imidazopyridines Chemical class 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 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 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 235000010356 sorbitol Nutrition 0.000 description 2
- 229960004793 sucrose Drugs 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 235000019364 tetracycline Nutrition 0.000 description 2
- 150000003522 tetracyclines Chemical class 0.000 description 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- SGKRLCUYIXIAHR-AKNGSSGZSA-N (4s,4ar,5s,5ar,6r,12ar)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1=CC=C2[C@H](C)[C@@H]([C@H](O)[C@@H]3[C@](C(O)=C(C(N)=O)C(=O)[C@H]3N(C)C)(O)C3=O)C3=C(O)C2=C1O SGKRLCUYIXIAHR-AKNGSSGZSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- YPELFRMCRYSPKZ-UHFFFAOYSA-N 4-amino-5-chloro-2-ethoxy-N-({4-[(4-fluorophenyl)methyl]morpholin-2-yl}methyl)benzamide Chemical compound CCOC1=CC(N)=C(Cl)C=C1C(=O)NCC1OCCN(CC=2C=CC(F)=CC=2)C1 YPELFRMCRYSPKZ-UHFFFAOYSA-N 0.000 description 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 1
- 229910000014 Bismuth subcarbonate Inorganic materials 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 208000007882 Gastritis Diseases 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- 229930182566 Gentamicin Natural products 0.000 description 1
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 1
- 229940122957 Histamine H2 receptor antagonist Drugs 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IQPSEEYGBUAQFF-UHFFFAOYSA-N Pantoprazole Chemical compound COC1=CC=NC(CS(=O)C=2NC3=CC=C(OC(F)F)C=C3N=2)=C1OC IQPSEEYGBUAQFF-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 208000008469 Peptic Ulcer Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 206010046274 Upper gastrointestinal haemorrhage Diseases 0.000 description 1
- 201000008629 Zollinger-Ellison syndrome Diseases 0.000 description 1
- 230000009858 acid secretion Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000000362 adenosine triphosphatase inhibitor Substances 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910021502 aluminium hydroxide Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229960004821 amikacin Drugs 0.000 description 1
- LKCWBDHBTVXHDL-RMDFUYIESA-N amikacin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1O LKCWBDHBTVXHDL-RMDFUYIESA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940126575 aminoglycoside Drugs 0.000 description 1
- 229960000723 ampicillin Drugs 0.000 description 1
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 1
- 229940069428 antacid Drugs 0.000 description 1
- 239000003159 antacid agent Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000001262 anti-secretory effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000003782 beta lactam antibiotic agent Substances 0.000 description 1
- 230000008827 biological function Effects 0.000 description 1
- 150000001621 bismuth Chemical class 0.000 description 1
- MGLUJXPJRXTKJM-UHFFFAOYSA-L bismuth subcarbonate Chemical compound O=[Bi]OC(=O)O[Bi]=O MGLUJXPJRXTKJM-UHFFFAOYSA-L 0.000 description 1
- 229940036358 bismuth subcarbonate Drugs 0.000 description 1
- 229960004645 bismuth subcitrate Drugs 0.000 description 1
- JAONZGLTYYUPCT-UHFFFAOYSA-K bismuth subgallate Chemical compound OC(=O)C1=CC(O)=C2O[Bi](O)OC2=C1 JAONZGLTYYUPCT-UHFFFAOYSA-K 0.000 description 1
- 229960000199 bismuth subgallate Drugs 0.000 description 1
- 229960001482 bismuth subnitrate Drugs 0.000 description 1
- ZREIPSZUJIFJNP-UHFFFAOYSA-K bismuth subsalicylate Chemical compound C1=CC=C2O[Bi](O)OC(=O)C2=C1 ZREIPSZUJIFJNP-UHFFFAOYSA-K 0.000 description 1
- 229960000782 bismuth subsalicylate Drugs 0.000 description 1
- ZQUAVILLCXTKTF-UHFFFAOYSA-H bismuth;tripotassium;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [K+].[K+].[K+].[Bi+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O ZQUAVILLCXTKTF-UHFFFAOYSA-H 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- QYIYFLOTGYLRGG-GPCCPHFNSA-N cefaclor Chemical compound C1([C@H](C(=O)N[C@@H]2C(N3C(=C(Cl)CS[C@@H]32)C(O)=O)=O)N)=CC=CC=C1 QYIYFLOTGYLRGG-GPCCPHFNSA-N 0.000 description 1
- 229960005361 cefaclor Drugs 0.000 description 1
- XIURVHNZVLADCM-IUODEOHRSA-N cefalotin Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)C(=O)CC1=CC=CS1 XIURVHNZVLADCM-IUODEOHRSA-N 0.000 description 1
- 229960000603 cefalotin Drugs 0.000 description 1
- OKBVVJOGVLARMR-QSWIMTSFSA-N cefixime Chemical compound S1C(N)=NC(C(=N\OCC(O)=O)\C(=O)N[C@@H]2C(N3C(=C(C=C)CS[C@@H]32)C(O)=O)=O)=C1 OKBVVJOGVLARMR-QSWIMTSFSA-N 0.000 description 1
- 229960002129 cefixime Drugs 0.000 description 1
- 229960005091 chloramphenicol Drugs 0.000 description 1
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229960001380 cimetidine Drugs 0.000 description 1
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 1
- 229960003405 ciprofloxacin Drugs 0.000 description 1
- DCSUBABJRXZOMT-IRLDBZIGSA-N cisapride Chemical compound C([C@@H]([C@@H](CC1)NC(=O)C=2C(=CC(N)=C(Cl)C=2)OC)OC)N1CCCOC1=CC=C(F)C=C1 DCSUBABJRXZOMT-IRLDBZIGSA-N 0.000 description 1
- 229960005132 cisapride Drugs 0.000 description 1
- DCSUBABJRXZOMT-UHFFFAOYSA-N cisapride Natural products C1CC(NC(=O)C=2C(=CC(N)=C(Cl)C=2)OC)C(OC)CN1CCCOC1=CC=C(F)C=C1 DCSUBABJRXZOMT-UHFFFAOYSA-N 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229960002626 clarithromycin Drugs 0.000 description 1
- 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 1
- 239000003086 colorant Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229960003722 doxycycline Drugs 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- IDYZIJYBMGIQMJ-UHFFFAOYSA-N enoxacin Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 IDYZIJYBMGIQMJ-UHFFFAOYSA-N 0.000 description 1
- 229960002549 enoxacin Drugs 0.000 description 1
- 229960003276 erythromycin Drugs 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- MVPICKVDHDWCJQ-UHFFFAOYSA-N ethyl 3-pyrrolidin-1-ylpropanoate Chemical compound CCOC(=O)CCN1CCCC1 MVPICKVDHDWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 210000004211 gastric acid Anatomy 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
- 230000001330 gastroprokinetic effect Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229960000318 kanamycin Drugs 0.000 description 1
- 229930027917 kanamycin Natural products 0.000 description 1
- SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 description 1
- 229930182823 kanamycin A Natural products 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229960003174 lansoprazole Drugs 0.000 description 1
- MJIHNNLFOKEZEW-UHFFFAOYSA-N lansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1 MJIHNNLFOKEZEW-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 229940041033 macrolides Drugs 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 235000019359 magnesium stearate Nutrition 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
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229960000282 metronidazole Drugs 0.000 description 1
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229960004085 mosapride Drugs 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229960000564 nitrofurantoin Drugs 0.000 description 1
- NXFQHRVNIOXGAQ-YCRREMRBSA-N nitrofurantoin Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)NC(=O)C1 NXFQHRVNIOXGAQ-YCRREMRBSA-N 0.000 description 1
- OGJPXUAPXNRGGI-UHFFFAOYSA-N norfloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 OGJPXUAPXNRGGI-UHFFFAOYSA-N 0.000 description 1
- 229960001180 norfloxacin Drugs 0.000 description 1
- 229960000381 omeprazole Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 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
- QGWDKKHSDXWPET-UHFFFAOYSA-E pentabismuth;oxygen(2-);nonahydroxide;tetranitrate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[O-2].[Bi+3].[Bi+3].[Bi+3].[Bi+3].[Bi+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O QGWDKKHSDXWPET-UHFFFAOYSA-E 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 208000000689 peptic esophagitis Diseases 0.000 description 1
- 208000011906 peptic ulcer disease Diseases 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000007660 quinolones Chemical class 0.000 description 1
- 229960004157 rabeprazole Drugs 0.000 description 1
- YREYEVIYCVEVJK-UHFFFAOYSA-N rabeprazole Chemical compound COCCCOC1=CC=NC(CS(=O)C=2NC3=CC=CC=C3N=2)=C1C YREYEVIYCVEVJK-UHFFFAOYSA-N 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
- 230000009467 reduction Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940045902 sodium stearyl fumarate Drugs 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
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
- C07D471/02—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 two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE9801526A SE9801526D0 (sv) | 1998-04-29 | 1998-04-29 | New compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200005796B true ZA200005796B (en) | 2002-01-18 |
Family
ID=20411154
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200005796A ZA200005796B (en) | 1998-04-29 | 2000-10-18 | Imidazo pyridine derivatives which inhibit gastric acid secretion. |
ZA200005797A ZA200005797B (en) | 1998-04-29 | 2000-10-18 | Imidazo pyridine derivatives which inhibit gastric acid secretion. |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200005797A ZA200005797B (en) | 1998-04-29 | 2000-10-18 | Imidazo pyridine derivatives which inhibit gastric acid secretion. |
Country Status (34)
Country | Link |
---|---|
US (2) | US6313137B1 (id) |
EP (4) | EP1073657B1 (id) |
JP (2) | JP3692034B2 (id) |
KR (3) | KR100595805B1 (id) |
CN (2) | CN1165535C (id) |
AR (2) | AR015768A1 (id) |
AT (4) | ATE312101T1 (id) |
AU (2) | AU769190B2 (id) |
BR (2) | BR9909995B1 (id) |
CA (2) | CA2329921A1 (id) |
CZ (2) | CZ292567B6 (id) |
DE (4) | DE69928792T2 (id) |
DK (2) | DK1073656T3 (id) |
EE (2) | EE04916B1 (id) |
ES (2) | ES2252975T3 (id) |
HK (5) | HK1033457A1 (id) |
HU (2) | HUP0102313A3 (id) |
ID (2) | ID26819A (id) |
IL (4) | IL139297A0 (id) |
IS (2) | IS5683A (id) |
MY (2) | MY121379A (id) |
NO (2) | NO318203B1 (id) |
NZ (2) | NZ507639A (id) |
PL (2) | PL343797A1 (id) |
RU (2) | RU2235725C2 (id) |
SA (2) | SA99200064B1 (id) |
SE (1) | SE9801526D0 (id) |
SI (1) | SI1073656T1 (id) |
SK (2) | SK285768B6 (id) |
TR (4) | TR200003176T2 (id) |
TW (2) | TWI250159B (id) |
UA (2) | UA66846C2 (id) |
WO (2) | WO1999055705A1 (id) |
ZA (2) | ZA200005796B (id) |
Families Citing this family (60)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6489346B1 (en) | 1996-01-04 | 2002-12-03 | The Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and method of using same |
US5840737A (en) | 1996-01-04 | 1998-11-24 | The Curators Of The University Of Missouri | Omeprazole solution and method for using same |
SE9802794D0 (sv) * | 1998-08-21 | 1998-08-21 | Astra Ab | New compounds |
US6900324B2 (en) | 2000-09-07 | 2005-05-31 | Astrazeneca Ab | Process for preparing a substituted imidazopyridine compound |
SE0003186D0 (sv) | 2000-09-07 | 2000-09-07 | Astrazeneca Ab | New process |
UA80393C2 (uk) | 2000-12-07 | 2007-09-25 | Алтана Фарма Аг | Фармацевтична композиція, яка містить інгібітор фде 4, диспергований в матриці |
SE0100297D0 (sv) * | 2001-02-01 | 2001-02-01 | Astrazeneca Ab | New compounds |
SE0100296D0 (sv) * | 2001-02-01 | 2001-02-01 | Astrazeneca Ab | New compounds |
SE0100295D0 (sv) * | 2001-02-01 | 2001-02-01 | Astrazeneca Ab | New compounds |
WO2002064121A1 (en) * | 2001-02-13 | 2002-08-22 | Astrazeneca Ab | Novel modified released formulation |
SK10982003A3 (sk) * | 2001-03-08 | 2004-02-03 | Astrazeneca Ab | Nové použitie |
SE0102808D0 (sv) * | 2001-08-22 | 2001-08-22 | Astrazeneca Ab | New compounds |
MY140561A (en) | 2002-02-20 | 2009-12-31 | Nycomed Gmbh | Dosage form containing pde 4 inhibitor as active ingredient |
SE0201940D0 (sv) * | 2002-06-20 | 2002-06-20 | Astrazeneca Ab | New combination II |
SE0201939D0 (sv) * | 2002-06-20 | 2002-06-20 | Astrazeneca Ab | New combination |
CA2499639C (en) | 2002-09-19 | 2011-11-08 | Schering Corporation | Imidazopyridines as cyclin dependent kinase inhibitors |
PL375567A1 (en) | 2002-11-19 | 2005-11-28 | Altana Pharma Ag | 8-substituted imidazopyridines |
AR043002A1 (es) * | 2003-02-18 | 2005-07-13 | Altana Pharma Ag | Imidazopirazinas 6-substituidos |
MXPA05009063A (es) * | 2003-02-26 | 2005-12-12 | Sugen Inc | Compuestos de aminoheteroarilo como inhibidores de proteina cinasa. |
RS20050669A (en) | 2003-03-10 | 2008-04-04 | Altana Pharma Ag., | Novel process for the preparation of roflumilast |
SE525349C2 (sv) * | 2003-06-23 | 2005-02-08 | Volvo Penta Ab | Utombordsdrev för båtar |
SE0301903D0 (sv) * | 2003-06-26 | 2003-06-26 | Astrazeneca Ab | Novel imidazopyridine compound III with therapeutic effect |
SE0301904D0 (sv) | 2003-06-26 | 2003-06-26 | Astrazeneca Ab | Novel imidazopyridine compound II with therapeutic effect |
SE0301905D0 (sv) * | 2003-06-26 | 2003-06-26 | Astrazeneca Ab | Novel imidazopyridine compound I with therapeutic effect |
US8993599B2 (en) | 2003-07-18 | 2015-03-31 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
WO2005041961A1 (en) * | 2003-11-03 | 2005-05-12 | Astrazeneca Ab | Imidazo [1,2-a] pyridine derivatives for the treatment of silent gastro-esophageal reflux |
SE0303451D0 (sv) * | 2003-12-18 | 2003-12-18 | Astrazeneca Ab | New compounds |
WO2005070927A2 (en) * | 2004-01-26 | 2005-08-04 | Altana Pharma Ag | 1,2,4-triazolo[1,5-a] pyridines as gastric acid secretion inhibitors |
US8906940B2 (en) | 2004-05-25 | 2014-12-09 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
AU2005315303A1 (en) * | 2004-12-17 | 2006-06-22 | Pfizer Inc. | Chromane derivatives useful as acid pump antagonists |
DK1861074T3 (da) | 2005-03-16 | 2013-07-29 | Takeda Gmbh | Smagsmaskeret doseringsform indeholdende roflumilast |
ES2470766T3 (es) * | 2005-03-21 | 2014-06-24 | Mei Pharma, Inc. | Derivados de [1,2-a]piridina: preparación y aplicaciones farmacéuticas |
US7666880B2 (en) | 2005-03-21 | 2010-02-23 | S*Bio Pte Ltd. | Imidazo[1,2-A]pyridine derivatives: preparation and pharmaceutical applications |
TW200700064A (en) * | 2005-03-24 | 2007-01-01 | Glaxo Group Ltd | Novel compounds |
GB0513423D0 (en) * | 2005-06-30 | 2005-08-03 | Glaxo Group Ltd | Novel compounds |
DK1959955T3 (da) * | 2005-12-05 | 2011-02-07 | Pfizer Prod Inc | Fremgangsmåde til behandling af abnorm cellevækst |
CA2632283C (en) | 2005-12-05 | 2011-06-21 | Pfizer Products Inc. | Polymorphs of a c-met/hgfr inhibitor |
JP2009530262A (ja) * | 2006-03-17 | 2009-08-27 | ラクオリア創薬株式会社 | クロマン誘導体 |
EP2054036B1 (en) | 2006-07-24 | 2019-12-18 | Singh-Broemer and Company, Inc. | Solid nanoparticle formulation of water insoluble pharmaceutical substances with reduced ostwald ripening |
WO2008059373A1 (en) * | 2006-11-17 | 2008-05-22 | Raqualia Pharma Inc. | Imidazo [1, 2-a] pyrazine derivatives and their use as acid pump antagonists |
EP1974729A1 (en) * | 2007-03-28 | 2008-10-01 | Santhera Pharmaceuticals (Schweiz) AG | Substituted imidazopyridine derivates as melanocortin- 4 receptor antagonists |
GB2471619B (en) * | 2008-03-31 | 2012-10-31 | Council Scient Ind Res | Method for the simultaneous preparation of 3-acetoxy-17-acetamdo-16-formyl-androst-5,16-diene and 3-acetoxy-2'-chloro-5-androsteno[17,6-B]pyridine |
AU2014201644B2 (en) * | 2008-12-03 | 2015-05-21 | Cinclus Pharma Holding AB (publ) | Imidazopyridine derivatives which inhibit the secretion of gastric acid |
FI20086158A0 (fi) | 2008-12-03 | 2008-12-03 | Mikael Dahlstroem | Imidatsopyridiinijohdannaiset |
WO2011004882A1 (ja) * | 2009-07-09 | 2011-01-13 | ラクオリア創薬株式会社 | 消化管運動異常が関与する疾患を治療するためのアシッドポンプ拮抗剤 |
WO2014209841A2 (en) * | 2013-06-25 | 2014-12-31 | F. Hoffmann-La Roche Ag | Compounds for treating spinal muscular atrophy |
AU2014365823B2 (en) | 2013-12-16 | 2019-05-02 | Abs Development 1, Inc. | P2X3 and/or P2X2/3 compounds and methods |
KR20160135234A (ko) * | 2014-03-24 | 2016-11-25 | 아르퀼 인코포레이티드 | 3-(3-(4-(1-아미노시클로부틸)페닐)-5-페닐-3h-이미다조[4,5-b]피리딘-2-일)피리딘-2-아민의 제조 방법 |
CN106279151A (zh) * | 2015-06-26 | 2017-01-04 | 江苏太瑞生诺生物医药科技有限公司 | 5-(2-(8-((2,6-二甲基苄基)氨基)-2,3-二甲基咪唑并[1,2-a]吡啶-6-甲酰胺基)乙氧基)-5-氧代戊酸的固体形式及其制备方法 |
KR101777971B1 (ko) * | 2016-07-05 | 2017-09-12 | 제일약품주식회사 | 이미다조[1,2-a]피리딘 유도체, 이의 제조방법 및 이의 용도 |
KR20190057569A (ko) | 2017-11-20 | 2019-05-29 | 제일약품주식회사 | 7-아미노-1h-인돌-5-카르복사미드 유도체 및 이의 용도 |
CN111683976B (zh) | 2018-02-05 | 2022-11-18 | 生物辐射实验室股份有限公司 | 具有阴离子交换-疏水混合模式配体的色谱树脂 |
WO2019197232A1 (de) | 2018-04-10 | 2019-10-17 | Bayer Aktiengesellschaft | Verfahren zur herstellung von 2,6-dialkylphenyl-essigsäuren |
RU2732297C2 (ru) * | 2018-11-14 | 2020-09-15 | Общество с ограниченной ответственностью "Гурус БиоФарм" | Производные нестероидных противовоспалительных средств |
MX2022005305A (es) | 2019-11-04 | 2022-08-16 | Cinclus Pharma Holding AB | Formulacion oral de x842. |
CN118201927A (zh) | 2021-11-05 | 2024-06-14 | 辛克鲁斯制药控股有限公司(Publ) | 戊二酸利那拉赞的盐酸盐的多晶型物 |
WO2023079093A1 (en) | 2021-11-05 | 2023-05-11 | Cinclus Pharma Holding AB (publ) | Polymorphs of the mesylate salt of linaprazan glurate |
KR102496869B1 (ko) * | 2022-07-29 | 2023-02-07 | 제일약품주식회사 | 이미다조[1,2-a]피리딘 화합물의 신규 염, 이의 결정형 및 제조방법 |
WO2024149833A1 (en) | 2023-01-11 | 2024-07-18 | Cinclus Pharma Holding AB (publ) | Polymorphs of the maleic acid salt of linaprazan glurate |
WO2024149834A1 (en) | 2023-01-11 | 2024-07-18 | Cinclus Pharma Holding AB (publ) | Polymorphs of the hydrobromide salt of linaprazan glurate |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ZA81219B (en) * | 1980-01-23 | 1982-01-27 | Schering Corp | Imidazo (1,2-a) pyridines ,process for their preparation and pharmaceutical compositions containing them |
EP0068378B1 (en) | 1981-06-26 | 1986-03-05 | Schering Corporation | Novel imidazo(1,2-a)pyridines and pyrazines, processes for their preparation and pharmaceutical compositions containing them |
US4725601A (en) * | 1985-06-04 | 1988-02-16 | Fujisawa Pharmaceutical Co., Ltd. | Certain imidazo[1,2-a]pyridines useful in the treatment of ulcers |
EP0228006A1 (en) * | 1985-12-16 | 1987-07-08 | Fujisawa Pharmaceutical Co., Ltd. | Imidazopyridine compounds and processes for preparation thereof |
GB8722488D0 (en) * | 1987-09-24 | 1987-10-28 | Fujisawa Pharmaceutical Co | Imidazopyridine compound |
-
1998
- 1998-04-29 SE SE9801526A patent/SE9801526D0/xx unknown
-
1999
- 1999-04-16 AR ARP990101776A patent/AR015768A1/es active IP Right Grant
- 1999-04-16 AR ARP990101777A patent/AR015769A1/es active IP Right Grant
- 1999-04-16 TW TW088106128A patent/TWI250159B/zh not_active IP Right Cessation
- 1999-04-16 TW TW088106129A patent/TW490466B/zh not_active IP Right Cessation
- 1999-04-23 CA CA002329921A patent/CA2329921A1/en not_active Abandoned
- 1999-04-23 KR KR1020057022787A patent/KR100595805B1/ko not_active IP Right Cessation
- 1999-04-23 PL PL99343797A patent/PL343797A1/xx unknown
- 1999-04-23 AT AT99947038T patent/ATE312101T1/de not_active IP Right Cessation
- 1999-04-23 EP EP99947038A patent/EP1073657B1/en not_active Expired - Lifetime
- 1999-04-23 EP EP04023090A patent/EP1491542B1/en not_active Expired - Lifetime
- 1999-04-23 EE EEP200000664A patent/EE04916B1/xx not_active IP Right Cessation
- 1999-04-23 AU AU43007/99A patent/AU769190B2/en not_active Ceased
- 1999-04-23 SK SK1492-2000A patent/SK285768B6/sk not_active IP Right Cessation
- 1999-04-23 NZ NZ507639A patent/NZ507639A/en unknown
- 1999-04-23 UA UA2000106034A patent/UA66846C2/uk unknown
- 1999-04-23 ID IDW20002206A patent/ID26819A/id unknown
- 1999-04-23 AT AT04023091T patent/ATE372340T1/de not_active IP Right Cessation
- 1999-04-23 NZ NZ507638A patent/NZ507638A/en unknown
- 1999-04-23 ES ES99947038T patent/ES2252975T3/es not_active Expired - Lifetime
- 1999-04-23 DK DK99947037T patent/DK1073656T3/da active
- 1999-04-23 US US09/319,973 patent/US6313137B1/en not_active Expired - Fee Related
- 1999-04-23 UA UA2000106033A patent/UA67769C2/uk unknown
- 1999-04-23 TR TR2000/03176T patent/TR200003176T2/xx unknown
- 1999-04-23 DE DE69928792T patent/DE69928792T2/de not_active Expired - Lifetime
- 1999-04-23 EP EP99947037A patent/EP1073656B1/en not_active Expired - Lifetime
- 1999-04-23 TR TR2001/02728T patent/TR200102728T2/xx unknown
- 1999-04-23 CA CA002329922A patent/CA2329922C/en not_active Expired - Fee Related
- 1999-04-23 HU HU0102313A patent/HUP0102313A3/hu unknown
- 1999-04-23 BR BRPI9909995-0A patent/BR9909995B1/pt not_active IP Right Cessation
- 1999-04-23 JP JP2000545865A patent/JP3692034B2/ja not_active Expired - Fee Related
- 1999-04-23 CZ CZ20003982A patent/CZ292567B6/cs not_active IP Right Cessation
- 1999-04-23 CN CNB998078026A patent/CN1165535C/zh not_active Expired - Fee Related
- 1999-04-23 TR TR2001/02612T patent/TR200102612T2/xx unknown
- 1999-04-23 AU AU43006/99A patent/AU769108B2/en not_active Ceased
- 1999-04-23 DK DK99947038T patent/DK1073657T3/da active
- 1999-04-23 BR BRPI9909996-9A patent/BR9909996B1/pt not_active IP Right Cessation
- 1999-04-23 DE DE69937077T patent/DE69937077T2/de not_active Expired - Lifetime
- 1999-04-23 JP JP2000545864A patent/JP3883383B2/ja not_active Expired - Fee Related
- 1999-04-23 WO PCT/SE1999/000662 patent/WO1999055705A1/en not_active Application Discontinuation
- 1999-04-23 DE DE69927803T patent/DE69927803T2/de not_active Expired - Lifetime
- 1999-04-23 RU RU2000127020/04A patent/RU2235725C2/ru active
- 1999-04-23 CZ CZ20003981A patent/CZ293977B6/cs not_active IP Right Cessation
- 1999-04-23 KR KR1020007012028A patent/KR100650472B1/ko not_active IP Right Cessation
- 1999-04-23 CN CNB998077992A patent/CN1174980C/zh not_active Expired - Fee Related
- 1999-04-23 ID IDW20002205A patent/ID27530A/id unknown
- 1999-04-23 AT AT99947037T patent/ATE307130T1/de not_active IP Right Cessation
- 1999-04-23 EP EP04023091A patent/EP1491543B1/en not_active Expired - Lifetime
- 1999-04-23 AT AT04023090T patent/ATE372339T1/de not_active IP Right Cessation
- 1999-04-23 TR TR2000/03149T patent/TR200003149T2/xx unknown
- 1999-04-23 WO PCT/SE1999/000663 patent/WO1999055706A1/en not_active Application Discontinuation
- 1999-04-23 PL PL343801A patent/PL195000B1/pl not_active IP Right Cessation
- 1999-04-23 HU HU0102425A patent/HUP0102425A3/hu unknown
- 1999-04-23 SK SK1491-2000A patent/SK14912000A3/sk unknown
- 1999-04-23 US US09/319,890 patent/US6313136B1/en not_active Expired - Fee Related
- 1999-04-23 EE EEP200000626A patent/EE04676B1/xx not_active IP Right Cessation
- 1999-04-23 IL IL13929799A patent/IL139297A0/xx active IP Right Grant
- 1999-04-23 SI SI9930850T patent/SI1073656T1/sl unknown
- 1999-04-23 IL IL13920099A patent/IL139200A0/xx unknown
- 1999-04-23 ES ES99947037T patent/ES2249913T3/es not_active Expired - Lifetime
- 1999-04-23 RU RU2000127019/04A patent/RU2238271C2/ru active
- 1999-04-23 KR KR1020007012027A patent/KR100595806B1/ko not_active IP Right Cessation
- 1999-04-23 DE DE69937076T patent/DE69937076T2/de not_active Expired - Lifetime
- 1999-04-27 MY MYPI99001650A patent/MY121379A/en unknown
- 1999-04-27 MY MYPI99001649A patent/MY121389A/en unknown
- 1999-05-01 SA SA99200064A patent/SA99200064B1/ar unknown
- 1999-05-01 SA SA99200065A patent/SA99200065B1/ar unknown
-
2000
- 2000-10-18 ZA ZA200005796A patent/ZA200005796B/en unknown
- 2000-10-18 ZA ZA200005797A patent/ZA200005797B/en unknown
- 2000-10-23 IL IL139200A patent/IL139200A/en not_active IP Right Cessation
- 2000-10-25 IS IS5683A patent/IS5683A/is unknown
- 2000-10-25 IS IS5684A patent/IS5684A/is unknown
- 2000-10-26 IL IL139297A patent/IL139297A/en not_active IP Right Cessation
- 2000-10-27 NO NO20005451A patent/NO318203B1/no not_active IP Right Cessation
- 2000-10-27 NO NO20005450A patent/NO317262B1/no not_active IP Right Cessation
-
2001
- 2001-06-12 HK HK01104026A patent/HK1033457A1/xx not_active IP Right Cessation
- 2001-06-13 HK HK05103978A patent/HK1071139A1/xx not_active IP Right Cessation
- 2001-06-13 HK HK01104064A patent/HK1033317A1/xx not_active IP Right Cessation
- 2001-11-07 HK HK01107808A patent/HK1036981A1/xx not_active IP Right Cessation
- 2001-11-08 HK HK01107857A patent/HK1036984A1/xx not_active IP Right Cessation
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
ZA200005796B (en) | Imidazo pyridine derivatives which inhibit gastric acid secretion. | |
EP1105390B1 (en) | Imidazo[1,2-a]pyridine derivatives for the treatment of gastrointestinal diseases | |
ZA200100913B (en) | New compounds. | |
US20040220209A1 (en) | Novel imidazopyridine compounds with therapeutic effect | |
ZA200609818B (en) | Amino-halogen-imidazopyridines as proton pump inhibitors | |
AU2002324402A1 (en) | Novel imidazopyridine compounds with therapeutic effect | |
MXPA00010231A (en) | Imidazo pyridine derivatives which inhibit gastric acid secretion |