NO860830L - - Google Patents
Info
- Publication number
- NO860830L NO860830L NO860830A NO860830A NO860830L NO 860830 L NO860830 L NO 860830L NO 860830 A NO860830 A NO 860830A NO 860830 A NO860830 A NO 860830A NO 860830 L NO860830 L NO 860830L
- Authority
- NO
- Norway
- Prior art keywords
- methoxy
- methyl
- benzimidazole
- compounds
- compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 113
- -1 pyrrolidino- Chemical class 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 60
- 238000000034 method Methods 0.000 description 55
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- 239000003153 chemical reaction reagent Substances 0.000 description 41
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 40
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 38
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
- 239000000203 mixture Substances 0.000 description 30
- 238000002360 preparation method Methods 0.000 description 29
- 239000000243 solution Substances 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 229910052739 hydrogen Inorganic materials 0.000 description 18
- 239000001257 hydrogen Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 17
- FOPXFYNQSUZLFU-UHFFFAOYSA-N 6-[(6-methoxy-1h-benzimidazol-2-yl)sulfanylmethyl]-n,n-dimethylpyrimidin-4-amine Chemical compound N=1C2=CC(OC)=CC=C2NC=1SCC1=CC(N(C)C)=NC=N1 FOPXFYNQSUZLFU-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 12
- 239000000284 extract Substances 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 108091006112 ATPases Proteins 0.000 description 9
- 102000057290 Adenosine Triphosphatases Human genes 0.000 description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
- 229910052736 halogen Inorganic materials 0.000 description 9
- 150000002367 halogens Chemical class 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- BFLXBWRDXMAVQI-UHFFFAOYSA-N 4-(chloromethyl)-5-methyl-6-piperidin-1-ylpyrimidine;hydrochloride Chemical compound Cl.CC1=C(CCl)N=CN=C1N1CCCCC1 BFLXBWRDXMAVQI-UHFFFAOYSA-N 0.000 description 8
- OWBOLAVFBHKZQQ-UHFFFAOYSA-N 4-(methoxymethyl)-5-methyl-6-piperidin-1-ylpyrimidine Chemical compound COCC1=NC=NC(N2CCCCC2)=C1C OWBOLAVFBHKZQQ-UHFFFAOYSA-N 0.000 description 8
- ZWKNZMVFHBDTDY-UHFFFAOYSA-N 6-methoxy-2-[(5-methyl-6-piperidin-1-ylpyrimidin-4-yl)methylsulfanyl]-1h-benzimidazole Chemical compound N1C2=CC(OC)=CC=C2N=C1SCC(C=1C)=NC=NC=1N1CCCCC1 ZWKNZMVFHBDTDY-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 239000011734 sodium Substances 0.000 description 7
- UFOZKQNDSVJNGS-UHFFFAOYSA-N (5-methyl-6-piperidin-1-ylpyrimidin-4-yl)methanol Chemical compound CC1=C(CO)N=CN=C1N1CCCCC1 UFOZKQNDSVJNGS-UHFFFAOYSA-N 0.000 description 6
- UQVFDJMABYSNMW-UHFFFAOYSA-N 4-chloro-2-(methoxymethyl)pyrimidine Chemical compound COCC1=NC=CC(Cl)=N1 UQVFDJMABYSNMW-UHFFFAOYSA-N 0.000 description 6
- QWACMTXPQTWMOA-UHFFFAOYSA-N 6-methoxy-2-[(4-piperidin-1-ylpyrimidin-2-yl)methylsulfanyl]-1h-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1SCC(N=1)=NC=CC=1N1CCCCC1 QWACMTXPQTWMOA-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 210000001156 gastric mucosa Anatomy 0.000 description 6
- ABCZTZZQNBWGLU-UHFFFAOYSA-N 6-methoxy-2-[(4-piperidin-1-ylpyrimidin-2-yl)methylsulfinyl]-1h-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC(N=1)=NC=CC=1N1CCCCC1 ABCZTZZQNBWGLU-UHFFFAOYSA-N 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 229960000212 aminophenazone Drugs 0.000 description 5
- 230000027119 gastric acid secretion Effects 0.000 description 5
- 210000004907 gland Anatomy 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 238000010561 standard procedure Methods 0.000 description 5
- ZKKKFIYVRQWMNU-UHFFFAOYSA-N (4-morpholin-4-ylpyrimidin-2-yl)methanol Chemical compound OCC1=NC=CC(N2CCOCC2)=N1 ZKKKFIYVRQWMNU-UHFFFAOYSA-N 0.000 description 4
- KCRYAXKYPOFNPX-UHFFFAOYSA-N 2-(methoxymethyl)-4-piperidin-1-ylpyrimidine Chemical compound COCC1=NC=CC(N2CCCCC2)=N1 KCRYAXKYPOFNPX-UHFFFAOYSA-N 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical group OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
- CEKXHQCCXLSOTR-UHFFFAOYSA-N 4-[2-(chloromethyl)pyrimidin-4-yl]morpholine;hydrochloride Chemical compound Cl.ClCC1=NC=CC(N2CCOCC2)=N1 CEKXHQCCXLSOTR-UHFFFAOYSA-N 0.000 description 4
- AEBNLCWJVOEKTF-UHFFFAOYSA-N 4-chloro-6-(methoxymethyl)-5-methylpyrimidine Chemical compound COCC1=NC=NC(Cl)=C1C AEBNLCWJVOEKTF-UHFFFAOYSA-N 0.000 description 4
- MUXKLXZFXWYORA-UHFFFAOYSA-N 6-methoxy-2-[(4-pyrrolidin-1-ylpyrimidin-2-yl)methylsulfanyl]-1h-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1SCC(N=1)=NC=CC=1N1CCCC1 MUXKLXZFXWYORA-UHFFFAOYSA-N 0.000 description 4
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical group 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 230000002496 gastric effect Effects 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- YIBCZHRGFVSCNI-UHFFFAOYSA-N 2-[(6-methoxy-1h-benzimidazol-2-yl)sulfanylmethyl]-n,n-dimethylpyrimidin-4-amine Chemical compound N=1C2=CC(OC)=CC=C2NC=1SCC1=NC=CC(N(C)C)=N1 YIBCZHRGFVSCNI-UHFFFAOYSA-N 0.000 description 3
- XGMVOHOJFJDWKK-UHFFFAOYSA-N 2-[(6-methoxy-1h-benzimidazol-2-yl)sulfinylmethyl]-n,n-dimethylpyrimidin-4-amine Chemical compound N1C2=CC(OC)=CC=C2N=C1S(=O)CC1=NC=CC(N(C)C)=N1 XGMVOHOJFJDWKK-UHFFFAOYSA-N 0.000 description 3
- QTEBICVJOMPLOG-UHFFFAOYSA-N 4-[2-[(6-methoxy-1h-benzimidazol-2-yl)sulfanylmethyl]pyrimidin-4-yl]morpholine Chemical compound N=1C2=CC(OC)=CC=C2NC=1SCC(N=1)=NC=CC=1N1CCOCC1 QTEBICVJOMPLOG-UHFFFAOYSA-N 0.000 description 3
- JYAWAGXRXIPNDJ-UHFFFAOYSA-N 4-[2-[(6-methoxy-1h-benzimidazol-2-yl)sulfinylmethyl]pyrimidin-4-yl]morpholine Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC(N=1)=NC=CC=1N1CCOCC1 JYAWAGXRXIPNDJ-UHFFFAOYSA-N 0.000 description 3
- OPAWKROMCNFVKJ-UHFFFAOYSA-N 4-[6-[(6-methoxy-1h-benzimidazol-2-yl)sulfanylmethyl]-5-methylpyrimidin-4-yl]morpholine Chemical compound N1C2=CC(OC)=CC=C2N=C1SCC(C=1C)=NC=NC=1N1CCOCC1 OPAWKROMCNFVKJ-UHFFFAOYSA-N 0.000 description 3
- BPHZVNFSDHAMNR-UHFFFAOYSA-N 4-[6-[(6-methoxy-1h-benzimidazol-2-yl)sulfinylmethyl]-5-methylpyrimidin-4-yl]morpholine Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC(C=1C)=NC=NC=1N1CCOCC1 BPHZVNFSDHAMNR-UHFFFAOYSA-N 0.000 description 3
- QOOQUMTZWQEHTR-UHFFFAOYSA-N 4-chloro-6-(methoxymethyl)pyrimidine Chemical compound COCC1=CC(Cl)=NC=N1 QOOQUMTZWQEHTR-UHFFFAOYSA-N 0.000 description 3
- KOFBRZWVWJCLGM-UHFFFAOYSA-N 5-methoxy-1,3-dihydrobenzimidazole-2-thione Chemical compound COC1=CC=C2NC(S)=NC2=C1 KOFBRZWVWJCLGM-UHFFFAOYSA-N 0.000 description 3
- RBZMXWLIRZOPEM-UHFFFAOYSA-N 6-(methoxymethyl)-5-methyl-1h-pyrimidin-4-one Chemical compound COCC1=NC=NC(O)=C1C RBZMXWLIRZOPEM-UHFFFAOYSA-N 0.000 description 3
- IMJDSMAGJSZBCF-UHFFFAOYSA-N 6-[(6-methoxy-1h-benzimidazol-2-yl)sulfanylmethyl]-n,n,5-trimethylpyrimidin-4-amine Chemical compound N1C2=CC(OC)=CC=C2N=C1SCC1=NC=NC(N(C)C)=C1C IMJDSMAGJSZBCF-UHFFFAOYSA-N 0.000 description 3
- MUFQHNUTHZTJEB-UHFFFAOYSA-N 6-[(6-methoxy-1h-benzimidazol-2-yl)sulfinylmethyl]-n,n-dimethylpyrimidin-4-amine Chemical compound N1C2=CC(OC)=CC=C2N=C1S(=O)CC1=CC(N(C)C)=NC=N1 MUFQHNUTHZTJEB-UHFFFAOYSA-N 0.000 description 3
- SRPYYNZHENIMMN-UHFFFAOYSA-N 6-methoxy-2-[(4-pyrrolidin-1-ylpyrimidin-2-yl)methylsulfinyl]-1h-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC(N=1)=NC=CC=1N1CCCC1 SRPYYNZHENIMMN-UHFFFAOYSA-N 0.000 description 3
- LDJXSPJQRPDQBN-UHFFFAOYSA-N 6-methoxy-2-[(5-methyl-6-piperidin-1-ylpyrimidin-4-yl)methylsulfinyl]-1h-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC(C=1C)=NC=NC=1N1CCCCC1 LDJXSPJQRPDQBN-UHFFFAOYSA-N 0.000 description 3
- NEWDAOWTMVCBJQ-UHFFFAOYSA-N 6-methoxy-2-[(5-methyl-6-pyrrolidin-1-ylpyrimidin-4-yl)methylsulfanyl]-1h-benzimidazole Chemical compound N1C2=CC(OC)=CC=C2N=C1SCC(C=1C)=NC=NC=1N1CCCC1 NEWDAOWTMVCBJQ-UHFFFAOYSA-N 0.000 description 3
- XZDCSXZWQCMHBJ-UHFFFAOYSA-N 6-methoxy-2-[(5-methyl-6-pyrrolidin-1-ylpyrimidin-4-yl)methylsulfinyl]-1h-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC(C=1C)=NC=NC=1N1CCCC1 XZDCSXZWQCMHBJ-UHFFFAOYSA-N 0.000 description 3
- NGEGVQDLJNHDGY-UHFFFAOYSA-N 6-methoxy-2-[(6-piperidin-1-ylpyrimidin-4-yl)methylsulfanyl]-1h-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1SCC(N=CN=1)=CC=1N1CCCCC1 NGEGVQDLJNHDGY-UHFFFAOYSA-N 0.000 description 3
- OAJSUSAJXVWPFM-UHFFFAOYSA-N 6-methoxy-2-[(6-piperidin-1-ylpyrimidin-4-yl)methylsulfinyl]-1h-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC(N=CN=1)=CC=1N1CCCCC1 OAJSUSAJXVWPFM-UHFFFAOYSA-N 0.000 description 3
- PALGJEGULANJFZ-UHFFFAOYSA-N 6-methoxy-2-[(6-pyrrolidin-1-ylpyrimidin-4-yl)methylsulfanyl]-1h-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1SCC(N=CN=1)=CC=1N1CCCC1 PALGJEGULANJFZ-UHFFFAOYSA-N 0.000 description 3
- ZBVQQOCPYJNPDO-UHFFFAOYSA-N 6-methoxy-2-[(6-pyrrolidin-1-ylpyrimidin-4-yl)methylsulfinyl]-1h-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC(N=CN=1)=CC=1N1CCCC1 ZBVQQOCPYJNPDO-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 208000007882 Gastritis Diseases 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 238000009825 accumulation Methods 0.000 description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000001262 anti-secretory effect Effects 0.000 description 3
- 150000001556 benzimidazoles Chemical class 0.000 description 3
- 159000000007 calcium salts Chemical class 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
- BYBVOZOPKGNZRX-UHFFFAOYSA-N (4-piperidin-1-ylpyrimidin-2-yl)methanol Chemical compound OCC1=NC=CC(N2CCCCC2)=N1 BYBVOZOPKGNZRX-UHFFFAOYSA-N 0.000 description 2
- ITKOJAUYZRYQFZ-UHFFFAOYSA-N (4-pyrrolidin-1-ylpyrimidin-2-yl)methanol Chemical compound OCC1=NC=CC(N2CCCC2)=N1 ITKOJAUYZRYQFZ-UHFFFAOYSA-N 0.000 description 2
- MKWVWKQTQSFIKP-UHFFFAOYSA-N (5-methyl-6-morpholin-4-ylpyrimidin-4-yl)methanol Chemical compound CC1=C(CO)N=CN=C1N1CCOCC1 MKWVWKQTQSFIKP-UHFFFAOYSA-N 0.000 description 2
- OPBHABICXKQUID-UHFFFAOYSA-N (5-methyl-6-pyrrolidin-1-ylpyrimidin-4-yl)methanol Chemical compound CC1=C(CO)N=CN=C1N1CCCC1 OPBHABICXKQUID-UHFFFAOYSA-N 0.000 description 2
- UPFMTQZLFRZBPQ-UHFFFAOYSA-N (6-piperidin-1-ylpyrimidin-4-yl)methanol Chemical compound C1=NC(CO)=CC(N2CCCCC2)=N1 UPFMTQZLFRZBPQ-UHFFFAOYSA-N 0.000 description 2
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- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- JYJVVHFRSFVEJM-UHFFFAOYSA-N iodosobenzene Chemical compound O=IC1=CC=CC=C1 JYJVVHFRSFVEJM-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 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
- 230000003902 lesion Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 210000004877 mucosa Anatomy 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([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
- 230000007935 neutral effect Effects 0.000 description 1
- 238000011587 new zealand white rabbit Methods 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010653 organometallic reaction Methods 0.000 description 1
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 1
- 150000002976 peresters Chemical class 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229960003531 phenolsulfonphthalein Drugs 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000011533 pre-incubation Methods 0.000 description 1
- 230000004224 protection Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 238000004062 sedimentation Methods 0.000 description 1
- 231100000161 signs of toxicity Toxicity 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003452 sulfinic acid derivatives Chemical class 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D491/02—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 two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB858505615A GB8505615D0 (en) | 1985-03-05 | 1985-03-05 | Heterocyclic compounds |
| GB858531605A GB8531605D0 (en) | 1985-12-23 | 1985-12-23 | Heterocyclic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO860830L true NO860830L (xx) | 1986-09-08 |
Family
ID=26288907
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO860830A NO860830L (xx) | 1985-03-05 | 1986-03-05 |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US4777172A (xx) |
| EP (1) | EP0198583A1 (xx) |
| CN (1) | CN86102398A (xx) |
| AU (1) | AU578141B2 (xx) |
| DK (2) | DK93986A (xx) |
| ES (1) | ES8707949A1 (xx) |
| FI (1) | FI860909A (xx) |
| GR (1) | GR860596B (xx) |
| HU (1) | HU195962B (xx) |
| IL (1) | IL78026A (xx) |
| JO (1) | JO1443B1 (xx) |
| NO (1) | NO860830L (xx) |
| NZ (1) | NZ215362A (xx) |
| PH (2) | PH23115A (xx) |
| PT (1) | PT82135B (xx) |
| ZW (1) | ZW4786A1 (xx) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0174717B1 (en) * | 1984-07-06 | 1992-01-22 | FISONS plc | Benzimidazoles, and their production formulation and use as gastric acid secretion inhibitors |
| DE3723327A1 (de) * | 1987-07-15 | 1989-02-02 | Hoechst Ag | Substituierte thienoimidazol-derivate, verfahren zu ihrer herstellung, sie enthaltende pharmazeutische zubereitungen und ihre verwendung als magensaeuresekretionshemmer, magenschutzmittel sowie als medikament gegen intestinale entzuendungen |
| DE4025387A1 (de) * | 1990-08-10 | 1992-02-13 | Hoechst Ag | Substituierte pyrimidin-derivate, verfahren zu ihrer herstellung und ihre verwendung als reagenzien |
| US6326384B1 (en) | 1999-08-26 | 2001-12-04 | Robert R. Whittle | Dry blend pharmaceutical unit dosage form |
| US6262086B1 (en) | 1999-08-26 | 2001-07-17 | Robert R. Whittle | Pharmaceutical unit dosage form |
| US6316020B1 (en) | 1999-08-26 | 2001-11-13 | Robert R. Whittle | Pharmaceutical formulations |
| US6312723B1 (en) | 1999-08-26 | 2001-11-06 | Robert R. Whittle | Pharmaceutical unit dosage form |
| US6268385B1 (en) | 1999-08-26 | 2001-07-31 | Robert R. Whittle | Dry blend pharmaceutical formulations |
| US6312712B1 (en) | 1999-08-26 | 2001-11-06 | Robert R. Whittle | Method of improving bioavailability |
| US6780880B1 (en) | 1999-08-26 | 2004-08-24 | Robert R. Whittle | FT-Raman spectroscopic measurement |
| US6262085B1 (en) | 1999-08-26 | 2001-07-17 | Robert R. Whittle | Alkoxy substituted Benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same |
| US6369087B1 (en) | 1999-08-26 | 2002-04-09 | Robert R. Whittle | Alkoxy substituted benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE416649B (sv) * | 1974-05-16 | 1981-01-26 | Haessle Ab | Forfarande for framstellning av foreningar som paverkar magsyrasekretionen |
| US4359465A (en) * | 1980-07-28 | 1982-11-16 | The Upjohn Company | Methods for treating gastrointestinal inflammation |
| EP0174717B1 (en) * | 1984-07-06 | 1992-01-22 | FISONS plc | Benzimidazoles, and their production formulation and use as gastric acid secretion inhibitors |
| EP0178438A1 (en) * | 1984-09-19 | 1986-04-23 | Beecham Group Plc | Novel compounds |
| FR2593178B1 (fr) * | 1986-01-20 | 1988-04-29 | Esteve Labor Dr | Derives de 2-benzimidazolylalkylthio (ou sulfinyle ou sulfonyle) leur preparation et leur application en tant que medicaments. |
-
0
- DK DK8600939D patent/DK8600939A/da unknown
-
1986
- 1986-02-14 US US06/829,366 patent/US4777172A/en not_active Expired - Fee Related
- 1986-02-26 JO JO19861443A patent/JO1443B1/en active
- 1986-02-26 ZW ZW47/86A patent/ZW4786A1/xx unknown
- 1986-02-27 AU AU54129/86A patent/AU578141B2/en not_active Ceased
- 1986-02-28 PH PH33460A patent/PH23115A/en unknown
- 1986-02-28 DK DK93986A patent/DK93986A/da not_active Application Discontinuation
- 1986-03-03 PT PT82135A patent/PT82135B/pt unknown
- 1986-03-03 EP EP86301493A patent/EP0198583A1/en not_active Withdrawn
- 1986-03-03 GR GR860596A patent/GR860596B/el unknown
- 1986-03-03 IL IL78026A patent/IL78026A/xx unknown
- 1986-03-04 NZ NZ215362A patent/NZ215362A/xx unknown
- 1986-03-04 ES ES552617A patent/ES8707949A1/es not_active Expired
- 1986-03-04 HU HU86885A patent/HU195962B/hu not_active IP Right Cessation
- 1986-03-04 FI FI860909A patent/FI860909A/fi not_active Application Discontinuation
- 1986-03-05 NO NO860830A patent/NO860830L/no unknown
- 1986-03-05 CN CN86102398A patent/CN86102398A/zh active Pending
-
1987
- 1987-06-17 PH PH35422A patent/PH23532A/en unknown
-
1988
- 1988-07-22 US US07/223,181 patent/US4820708A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| HUT40111A (en) | 1986-11-28 |
| PH23115A (en) | 1989-04-19 |
| JO1443B1 (en) | 1988-03-10 |
| PT82135A (en) | 1986-04-01 |
| CN86102398A (zh) | 1986-11-12 |
| EP0198583A1 (en) | 1986-10-22 |
| FI860909A (fi) | 1986-09-06 |
| NZ215362A (en) | 1989-01-06 |
| PT82135B (en) | 1988-06-24 |
| ES8707949A1 (es) | 1987-09-01 |
| GR860596B (en) | 1986-06-26 |
| HU195962B (en) | 1988-08-29 |
| ZW4786A1 (en) | 1987-09-16 |
| ES552617A0 (es) | 1987-09-01 |
| DK93986A (da) | 1986-09-06 |
| DK93986D0 (da) | 1986-02-28 |
| US4820708A (en) | 1989-04-11 |
| AU5412986A (en) | 1986-09-11 |
| IL78026A (en) | 1990-07-26 |
| AU578141B2 (en) | 1988-10-13 |
| FI860909A0 (fi) | 1986-03-04 |
| US4777172A (en) | 1988-10-11 |
| DK8600939A (xx) | 1986-09-06 |
| PH23532A (en) | 1989-08-25 |
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