RU2001123313A - Proton Pump Inhibitor Prodrugs - Google Patents
Proton Pump Inhibitor ProdrugsInfo
- Publication number
- RU2001123313A RU2001123313A RU2001123313/04A RU2001123313A RU2001123313A RU 2001123313 A RU2001123313 A RU 2001123313A RU 2001123313/04 A RU2001123313/04 A RU 2001123313/04A RU 2001123313 A RU2001123313 A RU 2001123313A RU 2001123313 A RU2001123313 A RU 2001123313A
- Authority
- RU
- Russia
- Prior art keywords
- pyridyl
- methoxy
- methyl
- benzimidazole
- sulfinyl
- Prior art date
Links
- 239000000651 prodrug Substances 0.000 title claims 4
- 229940002612 prodrugs Drugs 0.000 title claims 4
- 230000003482 proton pump inhibitor Effects 0.000 title claims 4
- 239000000612 proton pump inhibitor Substances 0.000 title claims 4
- -1 piperidino, morpholino Chemical group 0.000 claims 79
- 125000004432 carbon atoms Chemical group C* 0.000 claims 71
- 125000003545 alkoxy group Chemical group 0.000 claims 59
- 125000000217 alkyl group Chemical group 0.000 claims 47
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 32
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 22
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 18
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims 18
- 125000001072 heteroaryl group Chemical group 0.000 claims 17
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 16
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 12
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 10
- 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims 9
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 8
- 125000003282 alkyl amino group Chemical group 0.000 claims 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 7
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims 7
- 125000004414 alkyl thio group Chemical group 0.000 claims 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 claims 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 6
- 239000004202 carbamide Substances 0.000 claims 5
- 229910052801 chlorine Inorganic materials 0.000 claims 5
- 239000000460 chlorine Substances 0.000 claims 5
- 229910052731 fluorine Inorganic materials 0.000 claims 5
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 4
- 229910052794 bromium Inorganic materials 0.000 claims 4
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 4
- 125000004122 cyclic group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 125000005842 heteroatoms Chemical group 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000005242 carbamoyl alkyl group Chemical group 0.000 claims 3
- 150000002367 halogens Chemical group 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims 3
- 239000000546 pharmaceutic aid Substances 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N Imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 2
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 claims 2
- 125000003368 amide group Chemical group 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000001326 naphthylalkyl group Chemical group 0.000 claims 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000011780 sodium chloride Substances 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- QKPBGHHDSZRNQN-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonyl-5-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]benzimidazole Chemical compound COC1=CC=NC(CS(=O)C=2N(C3=CC=C(OC(F)F)C=C3N=2)S(=O)(=O)C=2C=CC(Br)=CC=2)=C1OC QKPBGHHDSZRNQN-UHFFFAOYSA-N 0.000 claims 1
- XVZLARUQGNQVON-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonyl-5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2N(S(=O)(=O)C=2C=CC(Br)=CC=2)C=1S(=O)CC1=NC=C(C)C(OC)=C1C XVZLARUQGNQVON-UHFFFAOYSA-N 0.000 claims 1
- GQQQWUNRBJQLJH-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonyl-6-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]benzimidazole Chemical compound COC1=CC=NC(CS(=O)C=2N(C3=CC(OC(F)F)=CC=C3N=2)S(=O)(=O)C=2C=CC(Br)=CC=2)=C1OC GQQQWUNRBJQLJH-UHFFFAOYSA-N 0.000 claims 1
- OCODMZPGXQZQKU-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonyl-6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]benzimidazole Chemical compound C12=CC(OC)=CC=C2N=C(S(=O)CC=2C(=C(OC)C(C)=CN=2)C)N1S(=O)(=O)C1=CC=C(Br)C=C1 OCODMZPGXQZQKU-UHFFFAOYSA-N 0.000 claims 1
- HTADVMJJTHPTFR-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfonyl-5-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]benzimidazole Chemical compound COC1=CC=NC(CS(=O)C=2N(C3=CC=C(OC(F)F)C=C3N=2)S(=O)(=O)C=2C=CC(Cl)=CC=2)=C1OC HTADVMJJTHPTFR-UHFFFAOYSA-N 0.000 claims 1
- KWRHZYCRMJTSRB-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfonyl-5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2N(S(=O)(=O)C=2C=CC(Cl)=CC=2)C=1S(=O)CC1=NC=C(C)C(OC)=C1C KWRHZYCRMJTSRB-UHFFFAOYSA-N 0.000 claims 1
- KYBPGUUFVPBWIU-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfonyl-6-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]benzimidazole Chemical compound COC1=CC=NC(CS(=O)C=2N(C3=CC(OC(F)F)=CC=C3N=2)S(=O)(=O)C=2C=CC(Cl)=CC=2)=C1OC KYBPGUUFVPBWIU-UHFFFAOYSA-N 0.000 claims 1
- DSPCRQZSDPGRRA-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfonyl-6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]benzimidazole Chemical compound C12=CC(OC)=CC=C2N=C(S(=O)CC=2C(=C(OC)C(C)=CN=2)C)N1S(=O)(=O)C1=CC=C(Cl)C=C1 DSPCRQZSDPGRRA-UHFFFAOYSA-N 0.000 claims 1
- MZGJQTZTAQDQLJ-UHFFFAOYSA-N 1-(4-fluorophenyl)sulfonyl-5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2N(S(=O)(=O)C=2C=CC(F)=CC=2)C=1S(=O)CC1=NC=C(C)C(OC)=C1C MZGJQTZTAQDQLJ-UHFFFAOYSA-N 0.000 claims 1
- BATRQZFXWCVVDQ-UHFFFAOYSA-N 1-(4-fluorophenyl)sulfonyl-6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]benzimidazole Chemical compound C12=CC(OC)=CC=C2N=C(S(=O)CC=2C(=C(OC)C(C)=CN=2)C)N1S(=O)(=O)C1=CC=C(F)C=C1 BATRQZFXWCVVDQ-UHFFFAOYSA-N 0.000 claims 1
- OKFRHDZMGCXUCM-UHFFFAOYSA-N 1-(benzenesulfonyl)-5-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]benzimidazole Chemical compound COC1=CC=NC(CS(=O)C=2N(C3=CC=C(OC(F)F)C=C3N=2)S(=O)(=O)C=2C=CC=CC=2)=C1OC OKFRHDZMGCXUCM-UHFFFAOYSA-N 0.000 claims 1
- LZHRKZDWTRCYQB-UHFFFAOYSA-N 1-(benzenesulfonyl)-5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2N(S(=O)(=O)C=2C=CC=CC=2)C=1S(=O)CC1=NC=C(C)C(OC)=C1C LZHRKZDWTRCYQB-UHFFFAOYSA-N 0.000 claims 1
- WCVQIXJVNSXQHZ-UHFFFAOYSA-N 1-(benzenesulfonyl)-6-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]benzimidazole Chemical compound COC1=CC=NC(CS(=O)C=2N(C3=CC(OC(F)F)=CC=C3N=2)S(=O)(=O)C=2C=CC=CC=2)=C1OC WCVQIXJVNSXQHZ-UHFFFAOYSA-N 0.000 claims 1
- HHOFJMXZAPJVOY-UHFFFAOYSA-N 1-(benzenesulfonyl)-6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]benzimidazole Chemical compound C12=CC(OC)=CC=C2N=C(S(=O)CC=2C(=C(OC)C(C)=CN=2)C)N1S(=O)(=O)C1=CC=CC=C1 HHOFJMXZAPJVOY-UHFFFAOYSA-N 0.000 claims 1
- SYNQSGIIZQHVRB-UHFFFAOYSA-N 2-[4-[2-[[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl]benzimidazol-1-yl]sulfonylphenoxy]-N-pyridin-2-ylacetamide Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1S(=O)(=O)C(C=C1)=CC=C1OCC(=O)NC1=CC=CC=N1 SYNQSGIIZQHVRB-UHFFFAOYSA-N 0.000 claims 1
- PQLOAZASLAZLIU-UHFFFAOYSA-N 2-[4-[2-[[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl]benzimidazol-1-yl]sulfonylphenoxy]-N-pyridin-2-ylacetamide Chemical compound COCCCOC1=CC=NC(CS(=O)C=2N(C3=CC=CC=C3N=2)S(=O)(=O)C=2C=CC(OCC(=O)NC=3N=CC=CC=3)=CC=2)=C1C PQLOAZASLAZLIU-UHFFFAOYSA-N 0.000 claims 1
- TVGCLWJMAGAPQZ-UHFFFAOYSA-N 2-[4-[5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]benzimidazol-1-yl]sulfonylphenoxy]acetamide Chemical compound N=1C2=CC(OC)=CC=C2N(S(=O)(=O)C=2C=CC(OCC(N)=O)=CC=2)C=1S(=O)CC1=NC=C(C)C(OC)=C1C TVGCLWJMAGAPQZ-UHFFFAOYSA-N 0.000 claims 1
- BIBHDKNXOGCAGL-UHFFFAOYSA-N 2-[4-[6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]benzimidazol-1-yl]sulfonylphenoxy]acetamide Chemical compound C12=CC(OC)=CC=C2N=C(S(=O)CC=2C(=C(OC)C(C)=CN=2)C)N1S(=O)(=O)C1=CC=C(OCC(N)=O)C=C1 BIBHDKNXOGCAGL-UHFFFAOYSA-N 0.000 claims 1
- QOXXWGFGORGMNU-UHFFFAOYSA-N 2-[[2-[4-[2-[[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl]benzimidazol-1-yl]sulfonylphenoxy]acetyl]amino]acetamide Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1S(=O)(=O)C1=CC=C(OCC(=O)NCC(N)=O)C=C1 QOXXWGFGORGMNU-UHFFFAOYSA-N 0.000 claims 1
- ZAQCQEQLSKIJTB-UHFFFAOYSA-N 4-[3-[4-[2-[[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl]benzimidazol-1-yl]sulfonylphenoxy]propyl]morpholine Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1S(=O)(=O)C(C=C1)=CC=C1OCCCN1CCOCC1 ZAQCQEQLSKIJTB-UHFFFAOYSA-N 0.000 claims 1
- WRXDMPKQXFBQKT-UHFFFAOYSA-N 4-[3-[4-[2-[[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl]benzimidazol-1-yl]sulfonylphenoxy]propyl]morpholine Chemical compound COCCCOC1=CC=NC(CS(=O)C=2N(C3=CC=CC=C3N=2)S(=O)(=O)C=2C=CC(OCCCN3CCOCC3)=CC=2)=C1C WRXDMPKQXFBQKT-UHFFFAOYSA-N 0.000 claims 1
- OAFCJDIXAFBMCQ-UHFFFAOYSA-N 4-[3-[4-[5-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]benzimidazol-1-yl]sulfonylphenoxy]propyl]morpholine Chemical compound COC1=CC=NC(CS(=O)C=2N(C3=CC=C(OC(F)F)C=C3N=2)S(=O)(=O)C=2C=CC(OCCCN3CCOCC3)=CC=2)=C1OC OAFCJDIXAFBMCQ-UHFFFAOYSA-N 0.000 claims 1
- KDLYDDQQFJGDQQ-UHFFFAOYSA-N 4-[3-[4-[5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]benzimidazol-1-yl]sulfonylphenoxy]propyl]morpholine Chemical compound N=1C2=CC(OC)=CC=C2N(S(=O)(=O)C=2C=CC(OCCCN3CCOCC3)=CC=2)C=1S(=O)CC1=NC=C(C)C(OC)=C1C KDLYDDQQFJGDQQ-UHFFFAOYSA-N 0.000 claims 1
- URVRCGCINSAWDE-UHFFFAOYSA-N 4-[3-[4-[6-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]benzimidazol-1-yl]sulfonylphenoxy]propyl]morpholine Chemical compound COC1=CC=NC(CS(=O)C=2N(C3=CC(OC(F)F)=CC=C3N=2)S(=O)(=O)C=2C=CC(OCCCN3CCOCC3)=CC=2)=C1OC URVRCGCINSAWDE-UHFFFAOYSA-N 0.000 claims 1
- JTMVEMUNUSXSGC-UHFFFAOYSA-N 4-[3-[4-[6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]benzimidazol-1-yl]sulfonylphenoxy]propyl]morpholine Chemical compound C12=CC(OC)=CC=C2N=C(S(=O)CC=2C(=C(OC)C(C)=CN=2)C)N1S(=O)(=O)C(C=C1)=CC=C1OCCCN1CCOCC1 JTMVEMUNUSXSGC-UHFFFAOYSA-N 0.000 claims 1
- SMEDQBSUFVTSFB-UHFFFAOYSA-N 4-[5-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]benzimidazol-1-yl]sulfonyl-N,N-dimethylaniline Chemical compound COC1=CC=NC(CS(=O)C=2N(C3=CC=C(OC(F)F)C=C3N=2)S(=O)(=O)C=2C=CC(=CC=2)N(C)C)=C1OC SMEDQBSUFVTSFB-UHFFFAOYSA-N 0.000 claims 1
- UXEJZQBFLLYQAQ-UHFFFAOYSA-N 4-[5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]benzimidazol-1-yl]sulfonyl-N,N-dimethylaniline Chemical compound N=1C2=CC(OC)=CC=C2N(S(=O)(=O)C=2C=CC(=CC=2)N(C)C)C=1S(=O)CC1=NC=C(C)C(OC)=C1C UXEJZQBFLLYQAQ-UHFFFAOYSA-N 0.000 claims 1
- FSNQNYOKVFFQMF-UHFFFAOYSA-N 5-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]-1-(4-fluorophenyl)sulfonylbenzimidazole Chemical compound COC1=CC=NC(CS(=O)C=2N(C3=CC=C(OC(F)F)C=C3N=2)S(=O)(=O)C=2C=CC(F)=CC=2)=C1OC FSNQNYOKVFFQMF-UHFFFAOYSA-N 0.000 claims 1
- FSULYPSMRGMGRX-UHFFFAOYSA-N 5-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]-1-(4-methoxyphenyl)sulfonylbenzimidazole Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C(OC(F)F)C=C2N=C1S(=O)CC1=NC=CC(OC)=C1OC FSULYPSMRGMGRX-UHFFFAOYSA-N 0.000 claims 1
- FYRYJARQBNAWSU-UHFFFAOYSA-N 5-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]-1-(4-methylphenyl)sulfonylbenzimidazole Chemical compound COC1=CC=NC(CS(=O)C=2N(C3=CC=C(OC(F)F)C=C3N=2)S(=O)(=O)C=2C=CC(C)=CC=2)=C1OC FYRYJARQBNAWSU-UHFFFAOYSA-N 0.000 claims 1
- DTQMZTGUNPFLOX-UHFFFAOYSA-N 5-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]-1-[3-(trifluoromethyl)phenyl]sulfonylbenzimidazole Chemical compound COC1=CC=NC(CS(=O)C=2N(C3=CC=C(OC(F)F)C=C3N=2)S(=O)(=O)C=2C=C(C=CC=2)C(F)(F)F)=C1OC DTQMZTGUNPFLOX-UHFFFAOYSA-N 0.000 claims 1
- LKOQHKJMOWHHNM-UHFFFAOYSA-N 5-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]-1-[4-(trifluoromethoxy)phenyl]sulfonylbenzimidazole Chemical compound COC1=CC=NC(CS(=O)C=2N(C3=CC=C(OC(F)F)C=C3N=2)S(=O)(=O)C=2C=CC(OC(F)(F)F)=CC=2)=C1OC LKOQHKJMOWHHNM-UHFFFAOYSA-N 0.000 claims 1
- BKJZNTODKIOOJC-UHFFFAOYSA-N 5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1-(4-methoxyphenyl)sulfonylbenzimidazole Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C(OC)C=C2N=C1S(=O)CC1=NC=C(C)C(OC)=C1C BKJZNTODKIOOJC-UHFFFAOYSA-N 0.000 claims 1
- FOHLVSARUQCCKV-UHFFFAOYSA-N 5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1-(4-methylphenyl)sulfonylbenzimidazole Chemical compound N=1C2=CC(OC)=CC=C2N(S(=O)(=O)C=2C=CC(C)=CC=2)C=1S(=O)CC1=NC=C(C)C(OC)=C1C FOHLVSARUQCCKV-UHFFFAOYSA-N 0.000 claims 1
- VKVNGZYEQFCSSG-UHFFFAOYSA-N 5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1-[3-(trifluoromethyl)phenyl]sulfonylbenzimidazole Chemical compound N=1C2=CC(OC)=CC=C2N(S(=O)(=O)C=2C=C(C=CC=2)C(F)(F)F)C=1S(=O)CC1=NC=C(C)C(OC)=C1C VKVNGZYEQFCSSG-UHFFFAOYSA-N 0.000 claims 1
- GDMCMXVKOBWLHV-UHFFFAOYSA-N 5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1-[4-(trifluoromethoxy)phenyl]sulfonylbenzimidazole Chemical compound N=1C2=CC(OC)=CC=C2N(S(=O)(=O)C=2C=CC(OC(F)(F)F)=CC=2)C=1S(=O)CC1=NC=C(C)C(OC)=C1C GDMCMXVKOBWLHV-UHFFFAOYSA-N 0.000 claims 1
- SGSYZYRAGIXDCI-UHFFFAOYSA-N 5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1-pyridin-3-ylsulfonylbenzimidazole Chemical compound N=1C2=CC(OC)=CC=C2N(S(=O)(=O)C=2C=NC=CC=2)C=1S(=O)CC1=NC=C(C)C(OC)=C1C SGSYZYRAGIXDCI-UHFFFAOYSA-N 0.000 claims 1
- QBJSJBBPMCXKET-UHFFFAOYSA-N 6-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]-1-(4-fluorophenyl)sulfonylbenzimidazole Chemical compound COC1=CC=NC(CS(=O)C=2N(C3=CC(OC(F)F)=CC=C3N=2)S(=O)(=O)C=2C=CC(F)=CC=2)=C1OC QBJSJBBPMCXKET-UHFFFAOYSA-N 0.000 claims 1
- MJLTWGHSAUAFES-UHFFFAOYSA-N 6-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]-1-(4-methoxyphenyl)sulfonylbenzimidazole Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC(OC(F)F)=CC=C2N=C1S(=O)CC1=NC=CC(OC)=C1OC MJLTWGHSAUAFES-UHFFFAOYSA-N 0.000 claims 1
- CFHWIZYZWBGDLR-UHFFFAOYSA-N 6-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]-1-(4-methylphenyl)sulfonylbenzimidazole Chemical compound COC1=CC=NC(CS(=O)C=2N(C3=CC(OC(F)F)=CC=C3N=2)S(=O)(=O)C=2C=CC(C)=CC=2)=C1OC CFHWIZYZWBGDLR-UHFFFAOYSA-N 0.000 claims 1
- AOUZYGOGHMEILX-UHFFFAOYSA-N 6-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]-1-[3-(trifluoromethyl)phenyl]sulfonylbenzimidazole Chemical compound COC1=CC=NC(CS(=O)C=2N(C3=CC(OC(F)F)=CC=C3N=2)S(=O)(=O)C=2C=C(C=CC=2)C(F)(F)F)=C1OC AOUZYGOGHMEILX-UHFFFAOYSA-N 0.000 claims 1
- NTDVEJJWURHVBF-UHFFFAOYSA-N 6-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]-1-[4-(trifluoromethoxy)phenyl]sulfonylbenzimidazole Chemical compound COC1=CC=NC(CS(=O)C=2N(C3=CC(OC(F)F)=CC=C3N=2)S(=O)(=O)C=2C=CC(OC(F)(F)F)=CC=2)=C1OC NTDVEJJWURHVBF-UHFFFAOYSA-N 0.000 claims 1
- BYRKVYORGOJWRL-UHFFFAOYSA-N 6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1-(4-methoxyphenyl)sulfonylbenzimidazole Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC(OC)=CC=C2N=C1S(=O)CC1=NC=C(C)C(OC)=C1C BYRKVYORGOJWRL-UHFFFAOYSA-N 0.000 claims 1
- AYPSXLNCBNPHKK-UHFFFAOYSA-N 6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1-(4-methylphenyl)sulfonylbenzimidazole Chemical compound C12=CC(OC)=CC=C2N=C(S(=O)CC=2C(=C(OC)C(C)=CN=2)C)N1S(=O)(=O)C1=CC=C(C)C=C1 AYPSXLNCBNPHKK-UHFFFAOYSA-N 0.000 claims 1
- JNRRSEJJTHKQPG-UHFFFAOYSA-N 6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1-[3-(trifluoromethyl)phenyl]sulfonylbenzimidazole Chemical compound C12=CC(OC)=CC=C2N=C(S(=O)CC=2C(=C(OC)C(C)=CN=2)C)N1S(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 JNRRSEJJTHKQPG-UHFFFAOYSA-N 0.000 claims 1
- WEWUITRNCCEAFP-UHFFFAOYSA-N 6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1-[4-(trifluoromethoxy)phenyl]sulfonylbenzimidazole Chemical compound C12=CC(OC)=CC=C2N=C(S(=O)CC=2C(=C(OC)C(C)=CN=2)C)N1S(=O)(=O)C1=CC=C(OC(F)(F)F)C=C1 WEWUITRNCCEAFP-UHFFFAOYSA-N 0.000 claims 1
- FPJMGWATBGVMSB-UHFFFAOYSA-N 6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1-pyridin-3-ylsulfonylbenzimidazole Chemical compound C12=CC(OC)=CC=C2N=C(S(=O)CC=2C(=C(OC)C(C)=CN=2)C)N1S(=O)(=O)C1=CC=CN=C1 FPJMGWATBGVMSB-UHFFFAOYSA-N 0.000 claims 1
- PRCFUGJWLMXLTK-UHFFFAOYSA-N 6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1-thiophen-2-ylsulfonylbenzimidazole Chemical compound C12=CC(OC)=CC=C2N=C(S(=O)CC=2C(=C(OC)C(C)=CN=2)C)N1S(=O)(=O)C1=CC=CS1 PRCFUGJWLMXLTK-UHFFFAOYSA-N 0.000 claims 1
- JYZIHLWOWKMNNX-UHFFFAOYSA-N Benzimidazole Chemical compound C1=C[CH]C2=NC=NC2=C1 JYZIHLWOWKMNNX-UHFFFAOYSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- MYICVUSHUPSZDM-UHFFFAOYSA-N N,N-dimethyl-2-[[1-[4-(2-morpholin-4-ylethoxy)phenyl]sulfonylbenzimidazol-2-yl]sulfinylmethyl]aniline Chemical compound CN(C)C1=CC=CC=C1CS(=O)C1=NC2=CC=CC=C2N1S(=O)(=O)C(C=C1)=CC=C1OCCN1CCOCC1 MYICVUSHUPSZDM-UHFFFAOYSA-N 0.000 claims 1
- OZJNANJEQMLRAH-UHFFFAOYSA-N N-[4-[5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]benzimidazol-1-yl]sulfonylphenyl]acetamide Chemical compound N=1C2=CC(OC)=CC=C2N(S(=O)(=O)C=2C=CC(NC(C)=O)=CC=2)C=1S(=O)CC1=NC=C(C)C(OC)=C1C OZJNANJEQMLRAH-UHFFFAOYSA-N 0.000 claims 1
- LLVWFYHDDUXYJG-UHFFFAOYSA-N N-[4-[6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]benzimidazol-1-yl]sulfonylphenyl]acetamide Chemical compound C12=CC(OC)=CC=C2N=C(S(=O)CC=2C(=C(OC)C(C)=CN=2)C)N1S(=O)(=O)C1=CC=C(NC(C)=O)C=C1 LLVWFYHDDUXYJG-UHFFFAOYSA-N 0.000 claims 1
- OTCUJODTBQNKHQ-UHFFFAOYSA-N N-[5-[6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]benzimidazol-1-yl]sulfonyl-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound C12=CC(OC)=CC=C2N=C(S(=O)CC=2C(=C(OC)C(C)=CN=2)C)N1S(=O)(=O)C=1SC(NC(C)=O)=NC=1C OTCUJODTBQNKHQ-UHFFFAOYSA-N 0.000 claims 1
- ZUWLAGPCNWNWQF-UHFFFAOYSA-N [4-[2-[[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl]benzimidazol-1-yl]sulfonylphenyl]urea Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1S(=O)(=O)C1=CC=C(NC(N)=O)C=C1 ZUWLAGPCNWNWQF-UHFFFAOYSA-N 0.000 claims 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 1
- 150000001556 benzimidazoles Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- BJOYCFXBRLSONQ-UHFFFAOYSA-N ethyl 4-[5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]benzimidazol-1-yl]sulfonylbenzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1S(=O)(=O)N1C2=CC=C(OC)C=C2N=C1S(=O)CC1=NC=C(C)C(OC)=C1C BJOYCFXBRLSONQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims 1
- 239000011737 fluorine Chemical group 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000002071 phenylalkoxy group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- GETQZCLCWQTVFV-UHFFFAOYSA-O trimethylammonium Chemical compound C[NH+](C)C GETQZCLCWQTVFV-UHFFFAOYSA-O 0.000 claims 1
- 0 Cc(cnc(CS(c1nc(cc(cc2)OC)c2[n]1*I)=O)c1C)c1OC Chemical compound Cc(cnc(CS(c1nc(cc(cc2)OC)c2[n]1*I)=O)c1C)c1OC 0.000 description 1
Claims (18)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/131,481 | 1998-08-10 | ||
US36438199A | 1999-07-29 | 1999-07-29 | |
US09/364,381 | 1999-07-29 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU2001107009 Division | 1999-08-09 |
Publications (2)
Publication Number | Publication Date |
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RU2001123313A true RU2001123313A (en) | 2003-12-20 |
RU2232159C2 RU2232159C2 (en) | 2004-07-10 |
Family
ID=33415733
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU2001123313/04A RU2232159C2 (en) | 1999-07-29 | 1999-08-09 | Derivatives of benzimidazole and pharmaceutical compositions comprising prodrug of proton pump inhibitor |
Country Status (1)
Country | Link |
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RU (1) | RU2232159C2 (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101687848B (en) * | 2006-12-29 | 2013-05-15 | 一洋药品株式会社 | Solid state forms of racemic ilaprazole |
-
1999
- 1999-08-09 RU RU2001123313/04A patent/RU2232159C2/en not_active IP Right Cessation
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