FI117672B - Menetelmä substituoitujen sulfoksidien syntetisoimiseksi - Google Patents
Menetelmä substituoitujen sulfoksidien syntetisoimiseksi Download PDFInfo
- Publication number
- FI117672B FI117672B FI970102A FI970102A FI117672B FI 117672 B FI117672 B FI 117672B FI 970102 A FI970102 A FI 970102A FI 970102 A FI970102 A FI 970102A FI 117672 B FI117672 B FI 117672B
- Authority
- FI
- Finland
- Prior art keywords
- alkyl
- eller
- alkoxy
- chiral
- halogen
- Prior art date
Links
- 150000003462 sulfoxides Chemical class 0.000 title claims description 84
- 238000000034 method Methods 0.000 title claims description 79
- 230000002194 synthesizing effect Effects 0.000 title 1
- 239000000203 mixture Substances 0.000 claims description 93
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 90
- -1 sulfoxide compound Chemical class 0.000 claims description 64
- 150000001875 compounds Chemical class 0.000 claims description 61
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 57
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- 238000007254 oxidation reaction Methods 0.000 claims description 48
- 230000003647 oxidation Effects 0.000 claims description 47
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 46
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 40
- 239000010936 titanium Substances 0.000 claims description 37
- 125000003545 alkoxy group Chemical group 0.000 claims description 35
- 229910052719 titanium Inorganic materials 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 229910052736 halogen Inorganic materials 0.000 claims description 31
- 150000002367 halogens Chemical group 0.000 claims description 31
- 239000000047 product Substances 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 238000002360 preparation method Methods 0.000 claims description 29
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical group CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims description 28
- 150000002431 hydrogen Chemical class 0.000 claims description 25
- YSAVZVORKRDODB-PHDIDXHHSA-N diethyl (2r,3r)-2,3-dihydroxybutanedioate Chemical compound CCOC(=O)[C@H](O)[C@@H](O)C(=O)OCC YSAVZVORKRDODB-PHDIDXHHSA-N 0.000 claims description 22
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 230000015572 biosynthetic process Effects 0.000 claims description 16
- 238000003786 synthesis reaction Methods 0.000 claims description 16
- 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 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- YSAVZVORKRDODB-WDSKDSINSA-N diethyl tartrate Chemical compound CCOC(=O)[C@@H](O)[C@H](O)C(=O)OCC YSAVZVORKRDODB-WDSKDSINSA-N 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 239000012043 crude product Substances 0.000 claims description 11
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 11
- 238000002425 crystallisation Methods 0.000 claims description 10
- 230000008025 crystallization Effects 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 9
- 239000003446 ligand Substances 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000002071 phenylalkoxy group Chemical group 0.000 claims description 9
- 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 claims description 8
- 125000002971 oxazolyl group Chemical group 0.000 claims description 8
- 239000007800 oxidant agent Substances 0.000 claims description 8
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 6
- 238000007796 conventional method Methods 0.000 claims description 6
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 239000000543 intermediate Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 3
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 claims description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 230000001404 mediated effect Effects 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 235000002906 tartaric acid Nutrition 0.000 claims description 3
- 239000011975 tartaric acid Substances 0.000 claims description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 238000010411 cooking Methods 0.000 claims description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 2
- 239000002585 base Substances 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 125000004950 trifluoroalkyl group Chemical group 0.000 claims 5
- 229940079593 drug Drugs 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 239000003086 colorant Substances 0.000 claims 3
- 239000003623 enhancer Substances 0.000 claims 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 150000004703 alkoxides Chemical class 0.000 claims 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims 2
- 230000001590 oxidative effect Effects 0.000 claims 2
- FZNCGRZWXLXZSZ-CIQUZCHMSA-N Voglibose Chemical compound OCC(CO)N[C@H]1C[C@](O)(CO)[C@@H](O)[C@H](O)[C@H]1O FZNCGRZWXLXZSZ-CIQUZCHMSA-N 0.000 claims 1
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 230000000692 anti-sense effect Effects 0.000 claims 1
- 230000000890 antigenic effect Effects 0.000 claims 1
- 101150057842 choA gene Proteins 0.000 claims 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 1
- 230000001815 facial effect Effects 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000002386 leaching Methods 0.000 claims 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims 1
- 210000005036 nerve Anatomy 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- 239000003380 propellant Substances 0.000 claims 1
- 230000000069 prophylactic effect Effects 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 230000002103 transcriptional effect Effects 0.000 claims 1
- 230000003442 weekly effect Effects 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 80
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 54
- 239000000243 solution Substances 0.000 description 49
- 230000003287 optical effect Effects 0.000 description 47
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
- 238000007792 addition Methods 0.000 description 35
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- 238000011914 asymmetric synthesis Methods 0.000 description 30
- 150000003457 sulfones Chemical class 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000003756 stirring Methods 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 238000004458 analytical method Methods 0.000 description 17
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 16
- 238000001914 filtration Methods 0.000 description 16
- 239000003921 oil Substances 0.000 description 15
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000001704 evaporation Methods 0.000 description 13
- 230000008020 evaporation Effects 0.000 description 13
- 239000010410 layer Substances 0.000 description 13
- 150000003568 thioethers Chemical class 0.000 description 13
- 235000019439 ethyl acetate Nutrition 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 11
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 11
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 239000003480 eluent Substances 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 8
- RKOTXQYWCBGZLP-UHFFFAOYSA-N N-[(2,4-difluorophenyl)methyl]-2-ethyl-9-hydroxy-3-methoxy-1,8-dioxospiro[3H-pyrido[1,2-a]pyrazine-4,3'-oxolane]-7-carboxamide Chemical compound CCN1C(OC)C2(CCOC2)N2C=C(C(=O)NCC3=C(F)C=C(F)C=C3)C(=O)C(O)=C2C1=O RKOTXQYWCBGZLP-UHFFFAOYSA-N 0.000 description 8
- 238000000605 extraction Methods 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- 125000004434 sulfur atom Chemical group 0.000 description 8
- 238000000926 separation method Methods 0.000 description 7
- HBDKFZNDMVLSHM-UHFFFAOYSA-N 2-(pyridin-2-ylmethylsulfinyl)-1h-benzimidazole Chemical class N=1C2=CC=CC=C2NC=1S(=O)CC1=CC=CC=N1 HBDKFZNDMVLSHM-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000010626 work up procedure Methods 0.000 description 6
- XURCIPRUUASYLR-UHFFFAOYSA-N Omeprazole sulfide Chemical compound N=1C2=CC(OC)=CC=C2NC=1SCC1=NC=C(C)C(OC)=C1C XURCIPRUUASYLR-UHFFFAOYSA-N 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 238000003818 flash chromatography Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229960000381 omeprazole Drugs 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- POQMHHDKXWTFHB-UHFFFAOYSA-N 1-[5-[(4,5-diphenyl-1h-imidazol-2-yl)sulfinyl]pentyl]-3,5-dimethylpyrazole Chemical compound N1=C(C)C=C(C)N1CCCCCS(=O)C1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 POQMHHDKXWTFHB-UHFFFAOYSA-N 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- 150000003608 titanium Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- KTTRNVVCHLQVQW-UHFFFAOYSA-N 5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-2,3-dihydro-1h-benzimidazole Chemical class N1C2=CC(OC)=CC=C2NC1S(=O)CC1=NC=C(C)C(OC)=C1C KTTRNVVCHLQVQW-UHFFFAOYSA-N 0.000 description 3
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 3
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 3
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- UUPITLNVYVCTFW-UHFFFAOYSA-N 1-[5-[(4,5-diphenyl-1h-imidazol-2-yl)sulfanyl]pentyl]-3,5-dimethylpyrazole Chemical compound N1=C(C)C=C(C)N1CCCCCSC1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 UUPITLNVYVCTFW-UHFFFAOYSA-N 0.000 description 2
- DXXKSPXIYBQZNZ-UHFFFAOYSA-N 2-(1H-benzimidazol-2-ylsulfonylmethyl)-N-methyl-N-(2-methylpropyl)aniline Chemical compound C(C(C)C)N(C)C1=C(CS(=O)(=O)C=2NC3=C(N=2)C=CC=C3)C=CC=C1 DXXKSPXIYBQZNZ-UHFFFAOYSA-N 0.000 description 2
- JSSNZRRZJATBLR-UHFFFAOYSA-N 2-(1h-benzimidazol-2-ylsulfanylmethyl)-n-methyl-n-(2-methylpropyl)aniline Chemical compound CC(C)CN(C)C1=CC=CC=C1CSC1=NC2=CC=CC=C2N1 JSSNZRRZJATBLR-UHFFFAOYSA-N 0.000 description 2
- 102100027324 2-hydroxyacyl-CoA lyase 1 Human genes 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical class [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 101001009252 Homo sapiens 2-hydroxyacyl-CoA lyase 1 Proteins 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- LCKIEQZJEYYRIY-UHFFFAOYSA-N Titanium ion Chemical compound [Ti+4] LCKIEQZJEYYRIY-UHFFFAOYSA-N 0.000 description 2
- 150000001556 benzimidazoles Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 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 2
- GFDHSPQGYGSEBJ-UHFFFAOYSA-N methyl 2-[(3,4-dimethoxypyridin-2-yl)methylsulfanyl]-6-methyl-1h-benzimidazole-5-carboxylate Chemical compound N1C=2C=C(C)C(C(=O)OC)=CC=2N=C1SCC1=NC=CC(OC)=C1OC GFDHSPQGYGSEBJ-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000012064 sodium phosphate buffer Substances 0.000 description 2
- RRFCKCAQHRITRG-UHFFFAOYSA-N sodium;5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]benzimidazol-3-ide;hydrate Chemical compound O.[Na+].N=1C2=CC(OC)=CC=C2[N-]C=1S(=O)CC1=NC=C(C)C(OC)=C1C RRFCKCAQHRITRG-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ZUDZWKJBYZAGBS-QWWZWVQMSA-N (2r,3r)-4-ethoxy-2,3-dihydroxy-4-oxobutanoic acid Chemical compound CCOC(=O)[C@H](O)[C@@H](O)C(O)=O ZUDZWKJBYZAGBS-QWWZWVQMSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
- VCMADTQZCBWKAB-UHFFFAOYSA-N 1-benzylsulfanyl-4-methylbenzene Chemical compound C1=CC(C)=CC=C1SCC1=CC=CC=C1 VCMADTQZCBWKAB-UHFFFAOYSA-N 0.000 description 1
- PQZKJXSQHLOQRF-UHFFFAOYSA-N 1-chloro-5-(5-chloropentylsulfinyl)pentane Chemical class ClCCCCCS(=O)CCCCCCl PQZKJXSQHLOQRF-UHFFFAOYSA-N 0.000 description 1
- AIABEETXTKSDLE-UHFFFAOYSA-J 2,3-dihydroxybutanedioate;titanium(4+) Chemical compound [Ti+4].[O-]C(=O)C(O)C(O)C([O-])=O.[O-]C(=O)C(O)C(O)C([O-])=O AIABEETXTKSDLE-UHFFFAOYSA-J 0.000 description 1
- PSIREIZGKQBEEO-UHFFFAOYSA-N 2-(1h-benzimidazol-2-ylsulfinylmethyl)-n-methyl-n-(2-methylpropyl)aniline Chemical compound CC(C)CN(C)C1=CC=CC=C1CS(=O)C1=NC2=CC=CC=C2N1 PSIREIZGKQBEEO-UHFFFAOYSA-N 0.000 description 1
- HKCNUIFWUYPDBM-UHFFFAOYSA-N 2-(pyridin-2-ylmethylsulfonyl)-1h-benzimidazole Chemical class N=1C2=CC=CC=C2NC=1S(=O)(=O)CC1=CC=CC=N1 HKCNUIFWUYPDBM-UHFFFAOYSA-N 0.000 description 1
- CCHLMSUZHFPSFC-UHFFFAOYSA-N 2-[[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfanyl]-1h-benzimidazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CSC1=NC2=CC=CC=C2N1 CCHLMSUZHFPSFC-UHFFFAOYSA-N 0.000 description 1
- BSXAHDOWMOSVAP-UHFFFAOYSA-N 2-[[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfanyl]-1h-benzimidazole Chemical compound COCCCOC1=CC=NC(CSC=2NC3=CC=CC=C3N=2)=C1C BSXAHDOWMOSVAP-UHFFFAOYSA-N 0.000 description 1
- NGBURUFPSLPDJS-UHFFFAOYSA-N 2-[[4-(cyclopropylmethoxy)pyridin-2-yl]methylsulfanyl]-5-fluoro-5H-benzimidazole Chemical compound FC1C=C2C(=NC(=N2)SCC2=NC=CC(=C2)OCC2CC2)C=C1 NGBURUFPSLPDJS-UHFFFAOYSA-N 0.000 description 1
- KTXVWWXXGRAFKB-UHFFFAOYSA-N 2-[[4-(cyclopropylmethoxy)pyridin-2-yl]methylsulfanyl]-6-fluoro-1h-benzimidazole Chemical compound N=1C2=CC(F)=CC=C2NC=1SCC(N=CC=1)=CC=1OCC1CC1 KTXVWWXXGRAFKB-UHFFFAOYSA-N 0.000 description 1
- DIUOJMLXZJHNDR-UHFFFAOYSA-N 2-[[4-(cyclopropylmethoxy)pyridin-2-yl]methylsulfinyl]-6-fluoro-1h-benzimidazole Chemical compound N=1C2=CC(F)=CC=C2NC=1S(=O)CC(N=CC=1)=CC=1OCC1CC1 DIUOJMLXZJHNDR-UHFFFAOYSA-N 0.000 description 1
- FOTFMGNDPAPMPD-UHFFFAOYSA-N 2-[[4-(cyclopropylmethoxy)pyridin-2-yl]methylsulfonyl]-6-fluoro-1H-benzimidazole Chemical compound FC1=CC2=C(NC(=N2)S(=O)(=O)CC2=NC=CC(=C2)OCC2CC2)C=C1 FOTFMGNDPAPMPD-UHFFFAOYSA-N 0.000 description 1
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 description 1
- GMTAWLUJHGIUPU-UHFFFAOYSA-N 4,5-diphenyl-1,3-dihydroimidazole-2-thione Chemical compound N1C(S)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 GMTAWLUJHGIUPU-UHFFFAOYSA-N 0.000 description 1
- CPHGOBGXZQKCKI-UHFFFAOYSA-N 4,5-diphenyl-1h-imidazole Chemical compound N1C=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 CPHGOBGXZQKCKI-UHFFFAOYSA-N 0.000 description 1
- MHVSIFIJPLSGIB-UHFFFAOYSA-N 5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfanyl]-5H-benzimidazole Chemical compound COC1C=C2C(=NC(=N2)SCC2=NC=C(C(=C2C)OC)C)C=C1 MHVSIFIJPLSGIB-UHFFFAOYSA-N 0.000 description 1
- UKILEIRWOYBGEJ-UHFFFAOYSA-N 6-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfanyl]-1h-benzimidazole Chemical compound COC1=CC=NC(CSC=2NC3=CC(OC(F)F)=CC=C3N=2)=C1OC UKILEIRWOYBGEJ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- GDVPKQONYOBALE-UHFFFAOYSA-N C1(=CC=CC=C1)C=1N=C(NC=1C1=CC=CC=C1)CSCC=1NC(=C(N=1)C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)C=1N=C(NC=1C1=CC=CC=C1)CSCC=1NC(=C(N=1)C1=CC=CC=C1)C1=CC=CC=C1 GDVPKQONYOBALE-UHFFFAOYSA-N 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
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 102000001494 Sterol O-Acyltransferase Human genes 0.000 description 1
- 108010054082 Sterol O-acyltransferase Proteins 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229920002807 Thiomer Polymers 0.000 description 1
- BLOIXGFLXPCOGW-UHFFFAOYSA-N [Ti].[Sn] Chemical compound [Ti].[Sn] BLOIXGFLXPCOGW-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004296 chiral HPLC Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- PDTRBCTYOYMYKK-RFIDALOWSA-N diethyl (2r,3r)-2,3-dihydroxybutanedioate;(2r,3r)-2,3-diethyl-2,3-dihydroxybutanedioic acid Chemical compound CCOC(=O)[C@H](O)[C@@H](O)C(=O)OCC.CC[C@](O)(C(O)=O)[C@](O)(CC)C(O)=O PDTRBCTYOYMYKK-RFIDALOWSA-N 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000027119 gastric acid secretion Effects 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229960003174 lansoprazole Drugs 0.000 description 1
- 229950007395 leminoprazole Drugs 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- RFJGNWGMCBFYTP-UHFFFAOYSA-N methyl 2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]-6-methyl-1h-benzimidazole-5-carboxylate Chemical compound N1C=2C=C(C)C(C(=O)OC)=CC=2N=C1S(=O)CC1=NC=CC(OC)=C1OC RFJGNWGMCBFYTP-UHFFFAOYSA-N 0.000 description 1
- VHILIAIEEYLJNA-UHFFFAOYSA-N methyl p-tolyl sulfide Chemical compound CSC1=CC=C(C)C=C1 VHILIAIEEYLJNA-UHFFFAOYSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 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
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229960005019 pantoprazole Drugs 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- IKNCGYCHMGNBCP-UHFFFAOYSA-N propan-1-olate Chemical compound CCC[O-] IKNCGYCHMGNBCP-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 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
- 230000001105 regulatory effect Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/28—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9402510A SE504459C2 (sv) | 1994-07-15 | 1994-07-15 | Förfarande för framställning av substituerade sulfoxider |
| SE9402510 | 1994-07-15 | ||
| PCT/SE1995/000818 WO1996002535A1 (en) | 1994-07-15 | 1995-07-03 | Process for synthesis of substituted sulphoxides |
| SE9500818 | 1995-07-03 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI970102A0 FI970102A0 (fi) | 1997-01-10 |
| FI970102L FI970102L (fi) | 1997-01-10 |
| FI117672B true FI117672B (fi) | 2007-01-15 |
Family
ID=20394753
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI970102A FI117672B (fi) | 1994-07-15 | 1997-01-10 | Menetelmä substituoitujen sulfoksidien syntetisoimiseksi |
| FI970102D FI117830B (fi) | 1994-07-15 | 1997-01-10 | Menetelmä substituoitujen sulfoksidien syntetisoimiseksi |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI970102D FI117830B (fi) | 1994-07-15 | 1997-01-10 | Menetelmä substituoitujen sulfoksidien syntetisoimiseksi |
Country Status (41)
| Country | Link |
|---|---|
| US (1) | US5948789A (pl) |
| EP (1) | EP0773940B2 (pl) |
| JP (1) | JP3795917B2 (pl) |
| KR (1) | KR100356252B1 (pl) |
| CN (1) | CN1070489C (pl) |
| AR (1) | AR003443A1 (pl) |
| AT (1) | ATE242233T1 (pl) |
| AU (1) | AU688074B2 (pl) |
| BR (1) | BR9508292A (pl) |
| CA (1) | CA2193994C (pl) |
| CZ (1) | CZ297987B6 (pl) |
| DE (1) | DE69530987T3 (pl) |
| DK (1) | DK0773940T4 (pl) |
| DZ (1) | DZ1911A1 (pl) |
| EE (1) | EE03354B1 (pl) |
| EG (1) | EG24534A (pl) |
| ES (1) | ES2199998T5 (pl) |
| FI (2) | FI117672B (pl) |
| HR (1) | HRP950401B1 (pl) |
| HU (1) | HU226361B1 (pl) |
| IL (1) | IL114477A (pl) |
| IS (1) | IS1772B (pl) |
| MA (1) | MA23611A1 (pl) |
| MX (1) | MX9700358A (pl) |
| MY (1) | MY113180A (pl) |
| NO (1) | NO312101B1 (pl) |
| NZ (1) | NZ289959A (pl) |
| PL (1) | PL186342B1 (pl) |
| PT (1) | PT773940E (pl) |
| RU (1) | RU2157806C2 (pl) |
| SA (1) | SA95160294B1 (pl) |
| SE (1) | SE504459C2 (pl) |
| SI (1) | SI0773940T2 (pl) |
| SK (1) | SK284059B6 (pl) |
| TN (1) | TNSN95081A1 (pl) |
| TR (1) | TR199500861A2 (pl) |
| TW (1) | TW372971B (pl) |
| UA (1) | UA47409C2 (pl) |
| WO (1) | WO1996002535A1 (pl) |
| YU (1) | YU49475B (pl) |
| ZA (1) | ZA955724B (pl) |
Families Citing this family (156)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9301830D0 (sv) * | 1993-05-28 | 1993-05-28 | Ab Astra | New compounds |
| US6875872B1 (en) | 1993-05-28 | 2005-04-05 | Astrazeneca | Compounds |
| SE504459C2 (sv) * | 1994-07-15 | 1997-02-17 | Astra Ab | Förfarande för framställning av substituerade sulfoxider |
| US6489346B1 (en) * | 1996-01-04 | 2002-12-03 | The Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and method of using same |
| US6699885B2 (en) * | 1996-01-04 | 2004-03-02 | The Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and methods 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 |
| US6645988B2 (en) | 1996-01-04 | 2003-11-11 | Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and method of using same |
| SE510650C2 (sv) | 1997-05-30 | 1999-06-14 | Astra Ab | Ny förening |
| US6747155B2 (en) | 1997-05-30 | 2004-06-08 | Astrazeneca Ab | Process |
| SE510643C2 (sv) * | 1997-06-27 | 1999-06-14 | Astra Ab | Termodynamiskt stabil omeprazol natrium form B |
| PL337888A1 (en) | 1997-07-03 | 2000-09-11 | Du Pont Pharm Co | Imidazoprimidines and imidazopyridines for use in treating neurological disorders |
| US6174548B1 (en) | 1998-08-28 | 2001-01-16 | Andrx Pharmaceuticals, Inc. | Omeprazole formulation |
| SE9704183D0 (sv) * | 1997-11-14 | 1997-11-14 | Astra Ab | New process |
| US6096340A (en) * | 1997-11-14 | 2000-08-01 | Andrx Pharmaceuticals, Inc. | Omeprazole formulation |
| WO1999038513A1 (en) * | 1998-01-30 | 1999-08-05 | Sepracor Inc. | R-lansoprazole compositions and methods |
| WO1999055157A1 (en) * | 1998-04-30 | 1999-11-04 | Sepracor Inc. | R-rabeprazole compositions and methods |
| WO1999055158A1 (en) * | 1998-04-30 | 1999-11-04 | Sepracor Inc. | S-rabeprazole compositions and methods |
| US6365589B1 (en) | 1998-07-02 | 2002-04-02 | Bristol-Myers Squibb Pharma Company | Imidazo-pyridines, -pyridazines, and -triazines as corticotropin releasing factor antagonists |
| US6733778B1 (en) | 1999-08-27 | 2004-05-11 | Andrx Pharmaceuticals, Inc. | Omeprazole formulation |
| CN1087739C (zh) * | 1998-12-28 | 2002-07-17 | 中国科学院成都有机化学研究所 | 光学纯的苯并咪唑类抗消化性溃疡药物的包结拆分制备法 |
| SE9900274D0 (sv) * | 1999-01-28 | 1999-01-28 | Astra Ab | New compound |
| TWI289557B (en) | 1999-06-17 | 2007-11-11 | Takeda Chemical Industries Ltd | A crystal of a hydrate of (R)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole |
| PT1191025E (pt) | 1999-06-30 | 2005-09-30 | Takeda Pharmaceutical | Cristais de lansoprazol |
| WO2001014366A1 (en) * | 1999-08-25 | 2001-03-01 | Takeda Chemical Industries, Ltd. | Process for the preparation of optically active sulfoxide derivatives |
| US6312712B1 (en) | 1999-08-26 | 2001-11-06 | Robert R. Whittle | Method of improving bioavailability |
| US6268385B1 (en) | 1999-08-26 | 2001-07-31 | Robert R. Whittle | Dry blend pharmaceutical formulations |
| US6262086B1 (en) | 1999-08-26 | 2001-07-17 | Robert R. Whittle | Pharmaceutical unit dosage form |
| US6312723B1 (en) | 1999-08-26 | 2001-11-06 | Robert R. Whittle | Pharmaceutical unit dosage form |
| US6326384B1 (en) | 1999-08-26 | 2001-12-04 | Robert R. Whittle | Dry blend pharmaceutical unit dosage form |
| 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 |
| US6316020B1 (en) | 1999-08-26 | 2001-11-13 | Robert R. Whittle | Pharmaceutical formulations |
| US6780880B1 (en) | 1999-08-26 | 2004-08-24 | Robert R. Whittle | FT-Raman spectroscopic measurement |
| 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 |
| KR100775802B1 (ko) * | 2000-04-28 | 2007-11-12 | 다케다 야쿠힌 고교 가부시키가이샤 | 광학 활성 술폭시드 유도체의 제조 방법 |
| CN100562318C (zh) * | 2000-05-15 | 2009-11-25 | 武田药品工业株式会社 | 晶体的制备方法 |
| KR100869677B1 (ko) | 2000-05-15 | 2008-11-21 | 다케다 야쿠힌 고교 가부시키가이샤 | 결정의 제조방법 |
| JP5412023B2 (ja) | 2000-08-04 | 2014-02-12 | 武田薬品工業株式会社 | ベンズイミダゾール化合物の塩およびその用途 |
| ATE511508T1 (de) * | 2000-12-01 | 2011-06-15 | Takeda Pharmaceutical | Verfahren zur kristallisation von (r)- oder (s)- lansoprazol |
| WO2002083608A2 (en) * | 2001-04-13 | 2002-10-24 | Apsinterm Llc | Methods of preparing sulfinamide and sulfoxides |
| GB2376231A (en) * | 2001-06-06 | 2002-12-11 | Cipla Ltd | Benzimidazole-cyclodextrin inclusion complex |
| US20040006111A1 (en) * | 2002-01-25 | 2004-01-08 | Kenneth Widder | Transmucosal delivery of proton pump inhibitors |
| ES2286408T3 (es) | 2002-03-05 | 2007-12-01 | Astrazeneca Ab | Sales de alquilamonio de omeprazol e esomeprazol. |
| AU2003262375A1 (en) * | 2002-04-22 | 2003-11-03 | Sun Pharmaceutical Industries Limited | Optically active substituted pyridinylmethyl-sulphinyl-benzimidazole and salts |
| US7169793B2 (en) | 2002-06-27 | 2007-01-30 | Dr. Reddy's Laboratories Limited | Process for preparation of optically pure or optically enriched sulfoxide compounds, including amorphous esomeprazole and salts thereof |
| MY148805A (en) | 2002-10-16 | 2013-05-31 | Takeda Pharmaceutical | Controlled release preparation |
| EP2596791B1 (en) | 2002-10-16 | 2015-04-01 | Takeda Pharmaceutical Company Limited | Stable solid preparations |
| BR0315574A (pt) | 2002-10-22 | 2005-09-20 | Ranbaxy Lab Ltd | Forma amorfa de esomeprazol, composição farmacêutica contendo o mesmo e processo para sua preparação |
| DE10254167A1 (de) | 2002-11-20 | 2004-06-09 | Icon Genetics Ag | Verfahren zur Kontrolle von zellulären Prozessen in Pflanzen |
| CN100500660C (zh) * | 2002-12-06 | 2009-06-17 | 尼可姆公司 | 用于制备泮托拉唑(pantoprazole)的方法 |
| ES2383679T3 (es) * | 2002-12-06 | 2012-06-25 | Nycomed Gmbh | Procedimiento para la preparación de (S)-pantoprazol |
| ES2397380T3 (es) * | 2002-12-06 | 2013-03-06 | Takeda Gmbh | Procedimiento para preparar compuestos activos ópticamente puros |
| FR2848555B1 (fr) | 2002-12-16 | 2006-07-28 | Negma Gild | Enantiomere(-)du tenatoprazole et son application en therapeutique |
| AU2003288576A1 (en) * | 2002-12-16 | 2004-07-09 | Ranbaxy Laboratories Limited | Rabeprazole calcium |
| US7507829B2 (en) | 2002-12-19 | 2009-03-24 | Teva Pharmaceuticals Industries, Ltd | Solid states of pantoprazole sodium, processes for preparing them and processes for preparing known pantoprazole sodium hydrates |
| WO2004060263A2 (en) * | 2003-01-07 | 2004-07-22 | Ranbaxy Laboratories Limited | Magnesium salt of imidazole derivative |
| US20040248942A1 (en) * | 2003-02-20 | 2004-12-09 | Bonnie Hepburn | Novel formulation, omeprazole antacid complex-immediate release for rapid and sustained suppression of gastric acid |
| BRPI0407906A (pt) * | 2003-02-28 | 2006-02-14 | Ranbaxy Lab Ltd | polimorfos de s-omeprazol |
| WO2004080961A2 (en) * | 2003-03-12 | 2004-09-23 | Teva Pharmaceutical Industries Ltd. | Crystalline and amorphous solids of pantoprazole and processes for their preparation |
| JP4355703B2 (ja) * | 2003-03-13 | 2009-11-04 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 歯ぎしりの予防剤または治療剤 |
| FR2852956B1 (fr) * | 2003-03-28 | 2006-08-04 | Negma Gild | Procede de preparation enantioselective de derives de sulfoxydes |
| EP1608649A2 (fr) * | 2003-03-28 | 2005-12-28 | Sidem Pharma SA | Procede de preparation enantioselective de derives de sulfoxydes. |
| EP1633736A1 (en) * | 2003-05-05 | 2006-03-15 | Ranbaxy Laboratories Limited | Barium salt of benzimidazole derivative |
| US7683177B2 (en) | 2003-06-10 | 2010-03-23 | Teva Pharmaceutical Industries Ltd | Process for preparing 2-[(pyridinyl)methyl]sulfinyl-substituted benzimidazoles and novel chlorinated derivatives of pantoprazole |
| US8993599B2 (en) | 2003-07-18 | 2015-03-31 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
| SE0302382D0 (sv) | 2003-09-04 | 2003-09-04 | Astrazeneca Ab | New salts II |
| SE0302381D0 (sv) | 2003-09-04 | 2003-09-04 | Astrazeneca Ab | New salts I |
| WO2005054228A1 (en) * | 2003-12-05 | 2005-06-16 | Hetero Drugs Limited | A process for the preparation of substitited pyridinylmethylsulfinyl- benzimidazole enantiomers |
| SE0400410D0 (sv) | 2004-02-20 | 2004-02-20 | Astrazeneca Ab | New compounds |
| EP1740571B1 (en) * | 2004-04-28 | 2009-07-29 | Hetero Drugs Limited | A process for preparing pyridinylmethyl-1h- benzimidazole compounds in enantiomerically enriched form or as single enantiomers |
| US8906940B2 (en) | 2004-05-25 | 2014-12-09 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
| US8815916B2 (en) | 2004-05-25 | 2014-08-26 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
| ATE456566T1 (de) * | 2004-05-28 | 2010-02-15 | Hetero Drugs Ltd | Neue stereoselektive synthese von benzimidazolsulfoxiden |
| MXPA06013623A (es) * | 2004-06-02 | 2007-02-28 | Altana Pharma Ag | Procedimiento para la preparacion de compuestos piridin-2-ilmetilsulfinil-1h-benzimidazol. |
| US8461187B2 (en) | 2004-06-16 | 2013-06-11 | Takeda Pharmaceuticals U.S.A., Inc. | Multiple PPI dosage form |
| US20080249134A1 (en) * | 2004-06-24 | 2008-10-09 | Ursula Hohlneicher | New Esomeprazole Sodium Salt Crystal Modification |
| CN103121992A (zh) * | 2004-06-24 | 2013-05-29 | 阿斯利康(瑞典)有限公司 | 制备用于制备艾美拉唑钠盐的结晶修饰物的新方法 |
| FR2876101B1 (fr) * | 2004-10-05 | 2007-03-02 | Sidem Pharma Sa Sa | Procede de preparation enantioselective de derives de sulfoxydes |
| US7915422B2 (en) * | 2004-10-11 | 2011-03-29 | Ranbaxy Laboratories Limited | Processes for the preparation of substituted sulfoxides |
| US7592111B2 (en) * | 2004-11-05 | 2009-09-22 | Xerox Corporation | Imaging member |
| WO2006099810A1 (en) | 2005-03-25 | 2006-09-28 | Livzon Pharmaceutical Group Inc. | Substituted sulfoxide compounds, methods for preparing the same and use thereof |
| CN101098867B (zh) * | 2005-03-25 | 2010-08-11 | 丽珠医药集团股份有限公司 | 取代的亚砜类化合物和其制备方法及用途 |
| US20090298884A1 (en) * | 2005-05-06 | 2009-12-03 | Glenmark Generics Ltd. | Esomeprazole Strontium Salt, Process For Its Preparation and Pharmaceutical Compositions Containing Same |
| WO2006131338A2 (en) * | 2005-06-08 | 2006-12-14 | Lek Pharmaceuticals D.D. | Crystalline solvate of omeprazole sodium |
| US20070043085A1 (en) * | 2005-08-19 | 2007-02-22 | Glenmark Pharmaceuticals Limited | Process for the preparation of amorphous form of neutral esomeprazole |
| WO2007067128A1 (en) | 2005-12-05 | 2007-06-14 | Astrazeneca Ab | New process for the preparation of esomeprazole non-salt form |
| EP1801110A1 (en) | 2005-12-22 | 2007-06-27 | KRKA, tovarna zdravil, d.d., Novo mesto | Esomeprazole arginine salt |
| DE102005061720B3 (de) * | 2005-12-22 | 2006-10-19 | Ratiopharm Gmbh | Enantioselektive Herstellung von Benzimidazolderivaten und ihren Salzen |
| US7553857B2 (en) | 2005-12-23 | 2009-06-30 | Lek Pharmaceuticals D.D. | S-omeprazole magnesium |
| ATE428707T1 (de) | 2005-12-28 | 2009-05-15 | Union Quimico Farma | Verfahren zur herstellung des (s)-enantiomers von omeprazol |
| CN1810803B (zh) * | 2006-02-17 | 2010-11-17 | 中国科学院上海有机化学研究所 | 高对映体选择性制备(s)-奥美拉唑的方法 |
| US7579476B2 (en) * | 2006-02-24 | 2009-08-25 | Praktikatalyst Pharma, Llc | Transition metal mediated oxidation of hetero atoms in organic molecules coordinated to transition metals |
| US8063074B2 (en) * | 2006-05-04 | 2011-11-22 | Dr. Reddy's Laboratories Limited | Polymorphic forms of esomeprazole sodium |
| US7786309B2 (en) * | 2006-06-09 | 2010-08-31 | Apotex Pharmachem Inc. | Process for the preparation of esomeprazole and salts thereof |
| WO2008004245A1 (en) | 2006-07-05 | 2008-01-10 | Lupin Limited | Process for the preparation of optically pure or optically enriched enantiomers of sulphoxide compounds |
| US8173818B2 (en) | 2006-08-08 | 2012-05-08 | Jubilant Organosys Limited | Process for producing sulphoxide compounds |
| WO2008047681A1 (en) | 2006-10-13 | 2008-04-24 | Eisai R & D Management Co., Ltd. | Benzimidazole compound having gastric acid secretion inhibitory activity |
| JP2009196894A (ja) * | 2006-10-13 | 2009-09-03 | Eisai R & D Management Co Ltd | スルフィニルベンズイミダゾール化合物またはその塩の製造方法 |
| EP1947099A1 (en) | 2007-01-18 | 2008-07-23 | LEK Pharmaceuticals D.D. | Process for solvent removal from omeprazole salts |
| WO2008102145A2 (en) | 2007-02-21 | 2008-08-28 | Cipla Limited | Process for the preparation of esomeprazole magnesium dihydrate |
| RU2341524C1 (ru) * | 2007-05-02 | 2008-12-20 | Новосибирский институт органической химии им. Н.Н. Ворожцова СО РАН (НИОХ СО РАН) | СПОСОБ ПОЛУЧЕНИЯ ОПТИЧЕСКИ АКТИВНОГО 5-МЕТОКСИ-2-((4-МЕТОКСИ-3,5-ДИМЕТИЛПИРИДИН-2-ИЛ)МЕТИЛСУЛЬФИНИЛ)-1Н-БЕНЗО[d]ИМИДАЗОЛА |
| US8492551B2 (en) * | 2007-06-07 | 2013-07-23 | Aurobindo Pharma. Ltd. | Process for preparing an optically active proton pump inhibitor |
| CN101323609B (zh) * | 2007-06-15 | 2013-05-01 | 成都福瑞生物工程有限公司 | 不对称氧化硫醚成亚砜合成对映体含量高的苯并咪唑衍生物的方法 |
| WO2009066321A2 (en) * | 2007-10-03 | 2009-05-28 | Ipca Laboratories Limited | Process for optically active sulfoxide compounds |
| WO2009047775A2 (en) | 2007-10-08 | 2009-04-16 | Hetero Drugs Limited | Polymorphs of esomeprazole salts |
| SG185296A1 (en) | 2007-10-12 | 2012-11-29 | Takeda Pharmaceuticals Usa Inc | Methods of treating gastrointestinal disorders independent of the intake of food |
| FR2925899B1 (fr) * | 2007-12-27 | 2012-12-21 | Sidem Pharma Sa | Procede de preparation enantioselective de sulfoxydes. |
| CN101492459B (zh) * | 2008-01-25 | 2011-04-27 | 山东轩竹医药科技有限公司 | 含烷氧乙酰基二氢异噁唑并吡啶化合物 |
| CN101497603B (zh) * | 2008-01-30 | 2012-11-07 | 山东轩竹医药科技有限公司 | 含有被烷氧烷胺氧基取代的吡啶的苯并咪唑衍生物 |
| JP2011513202A (ja) | 2008-03-10 | 2011-04-28 | 武田薬品工業株式会社 | ベンズイミダゾール化合物の結晶 |
| US20110028518A1 (en) * | 2008-03-18 | 2011-02-03 | Dr. Reddy's Laboratories Ltd. | Dexlansoprazole process and polymorphs |
| CN101538264A (zh) * | 2008-03-19 | 2009-09-23 | 中国科学院成都有机化学有限公司 | 手性亚砜类化合物的制备新方法 |
| WO2009145368A1 (en) * | 2008-05-27 | 2009-12-03 | Sk Chemicals Co., Ltd. | Improved preparing method of (s)-omeprazole from omeprazole racemate using optical resolution agent |
| EP2143722A1 (en) | 2008-07-09 | 2010-01-13 | Lek Pharmaceuticals D.D. | Process for preparation of esomeprazole sodium of high chemical purity and new forms of esomeprazole sodium |
| WO2010039885A2 (en) * | 2008-09-30 | 2010-04-08 | Teva Pharmaceutical Industries Ltd. | Crystalline forms of dexlansoprazole |
| EP2264024A1 (en) | 2008-10-14 | 2010-12-22 | LEK Pharmaceuticals d.d. | Process for the preparation of enantiomerically enriched proton pump inhibitors |
| IT1391776B1 (it) | 2008-11-18 | 2012-01-27 | Dipharma Francis Srl | Procedimento per la preparazione di dexlansoprazolo |
| CZ200990A3 (cs) * | 2009-02-16 | 2010-08-25 | Zentiva, K.S. | Zpusob výroby (S)-5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazolu |
| WO2010097583A1 (en) | 2009-02-24 | 2010-09-02 | Cipla Limited | Esomeprazole potassium polymorph and its preparation |
| CZ2009172A3 (cs) * | 2009-03-17 | 2010-09-29 | Zentiva, K.S. | Zpusob výroby (S)-5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazolu |
| US20130030186A1 (en) * | 2009-06-02 | 2013-01-31 | Sun Pharmaceutical Industries Limited | Process for preparing sulphoxide compounds |
| IT1395118B1 (it) | 2009-07-29 | 2012-09-05 | Dipharma Francis Srl | Procedimento per la preparazione di dexlansoprazolo cristallino |
| EP2499125B1 (en) | 2009-11-12 | 2016-01-27 | Hetero Research Foundation | Process for the resolution of omeprazole |
| CA2788147A1 (en) | 2010-01-29 | 2011-08-04 | Ranbaxy Laboratories Limited | Process for the preparation of crystalline forms of dexlansoprazole |
| CA2803673A1 (en) | 2010-06-24 | 2011-12-29 | Cipla Limited | Salts and polymorphs of dexrabeprazole |
| CN101914090B (zh) * | 2010-08-13 | 2013-03-20 | 埃斯特维华义制药有限公司 | 左旋奥美拉唑的制备方法 |
| CN102558150B (zh) * | 2010-12-31 | 2014-03-12 | 正大天晴药业集团股份有限公司 | 取代亚砜化合物的合成方法 |
| CN102321071B (zh) * | 2011-07-20 | 2013-01-23 | 江苏奥赛康药业股份有限公司 | 一种高纯度埃索美拉唑钠的工业化生产方法 |
| CN102977076A (zh) * | 2011-09-02 | 2013-03-20 | 扬子江药业集团上海海尼药业有限公司 | 一种右兰索拉唑的制备方法 |
| CN102329302A (zh) * | 2011-10-22 | 2012-01-25 | 刘强 | 一种埃索美拉唑及其盐的制备方法 |
| CN102408412A (zh) * | 2011-10-25 | 2012-04-11 | 广东华南药业集团有限公司 | 高对映体选择性制备（s）- 奥美拉唑的方法 |
| CN102432412A (zh) * | 2011-10-28 | 2012-05-02 | 成都欣捷高新技术开发有限公司 | 一种手性亚砜类质子泵抑制剂或其可药用盐的制备方法 |
| KR101300950B1 (ko) * | 2011-10-31 | 2013-08-27 | 르노삼성자동차 주식회사 | 전기자동차의 공기 흡입 장치 |
| WO2013140120A1 (en) | 2012-03-22 | 2013-09-26 | Cipla Limited | Glycerol solvate forms of (r) - 2 - [ [ [3 -methyl -4 (2,2, 2 - trifluoroethoxy) pyridin- 2 - yl] methyl] sulphinyl] - 1h - ben zimidazole |
| CN102633776B (zh) * | 2012-03-28 | 2014-06-18 | 中山市仁合药业有限公司 | 一种埃索美拉唑及其钠盐的制备方法 |
| CN102659763B (zh) * | 2012-04-27 | 2014-01-22 | 南京优科生物医药研究有限公司 | 一种右旋兰索拉唑合成与纯化的方法 |
| CN103044402B (zh) * | 2012-12-31 | 2015-01-14 | 康普药业股份有限公司 | 埃索美拉唑钠合成生产方法 |
| CN103113351B (zh) * | 2013-03-08 | 2015-01-21 | 苏州特瑞药业有限公司 | 一种光学纯手性亚砜类化合物的制备方法 |
| CN104177336A (zh) * | 2013-05-28 | 2014-12-03 | 上海汇伦生命科技有限公司 | 一种对映选择性合成右兰索拉唑的方法 |
| US10130618B2 (en) | 2014-04-11 | 2018-11-20 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | Pharmaceutical combinations of dabigatran and proton pump inhibitors |
| WO2015155307A1 (en) | 2014-04-11 | 2015-10-15 | Sanovel Ilac Sanayi Ve Ticaret A.S. | Pharmaceutical combinations of rivaroxaban and proton pump inhibitors |
| EP2980086B1 (en) | 2014-07-29 | 2016-06-15 | F.I.S.- Fabbrica Italiana Sintetici S.p.A. | Efficient process for the preparation of esomeprazole (S)-binol complex |
| WO2016104668A1 (ja) * | 2014-12-26 | 2016-06-30 | 国立大学法人 東京大学 | 光学活性のプロトンポンプ阻害化合物の製造方法 |
| CN104610226A (zh) * | 2014-12-31 | 2015-05-13 | 广东东阳光药业有限公司 | 一种右兰索拉唑的不对称氧化方法 |
| EP3064495B1 (en) | 2015-03-06 | 2016-12-14 | F.I.S.- Fabbrica Italiana Sintetici S.p.A. | Improved process for the preparation of optically pure esomeprazole |
| CN105218392B (zh) * | 2015-07-09 | 2017-11-21 | 天津青松华药医药有限公司 | D‑酒石酸单酯单酰胺类化合物 |
| CN105218391B (zh) * | 2015-07-09 | 2017-11-21 | 天津青松华药医药有限公司 | L‑酒石酸单酯单酰胺类化合物 |
| CN105968097B (zh) * | 2016-05-17 | 2019-05-03 | 杭州华东医药集团新药研究院有限公司 | 左旋泮托拉唑的工业化生产方法 |
| CN106083818A (zh) * | 2016-06-08 | 2016-11-09 | 扬子江药业集团有限公司 | 一种高纯度埃索美拉唑钠的制备方法 |
| CN106366070B (zh) * | 2016-08-10 | 2019-06-11 | 上海万巷制药有限公司 | 一种高纯度埃索美拉唑钠的制备方法 |
| EP3512840B1 (en) * | 2016-09-14 | 2024-03-06 | Yufeng Jane Tseng | Novel substituted benzimidazole derivatives as d-amino acid oxidase (daao) inhibitors |
| CN106632248A (zh) * | 2016-09-30 | 2017-05-10 | 青岛云天生物技术有限公司 | 一种左旋泮托拉唑钠的制备工艺 |
| CN106632249A (zh) * | 2016-09-30 | 2017-05-10 | 青岛云天生物技术有限公司 | 一种制备(s)‑泮托拉唑钠的方法 |
| CN106866630B (zh) * | 2017-04-01 | 2018-08-07 | 上海华源医药科技发展有限公司 | 一种右兰索拉唑的制备方法 |
| CN110746428A (zh) * | 2019-10-29 | 2020-02-04 | 株洲千金药业股份有限公司 | 一种r型手性亚砜类化合物的制备方法 |
| CN110698482A (zh) * | 2019-10-29 | 2020-01-17 | 株洲千金药业股份有限公司 | 一种s型手性亚砜类化合物的制备方法 |
| CN113845510B (zh) * | 2020-06-27 | 2025-02-18 | 鲁南制药集团股份有限公司 | 一种埃索美拉唑的制备方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE7804231L (sv) * | 1978-04-14 | 1979-10-15 | Haessle Ab | Magsyrasekretionsmedel |
| JPS6150978A (ja) * | 1984-08-16 | 1986-03-13 | Takeda Chem Ind Ltd | ピリジン誘導体およびその製造法 |
| GB2189698A (en) * | 1986-04-30 | 1987-11-04 | Haessle Ab | Coated omeprazole tablets |
| SE9002206D0 (sv) * | 1990-06-20 | 1990-06-20 | Haessle Ab | New compounds |
| DE4035455A1 (de) * | 1990-11-08 | 1992-05-14 | Byk Gulden Lomberg Chem Fab | Enantiomerentrennung |
| WO1993006037A1 (en) * | 1991-09-16 | 1993-04-01 | Catalytica, Inc. | Process and catalyst for producing bromine |
| KR950701921A (ko) * | 1992-06-01 | 1995-05-17 | 고야 다다시 | 피리딘 화합물 및 이의 제약학적 용도(pyridine compound and medicinal use thereof) |
| SE9301830D0 (sv) * | 1993-05-28 | 1993-05-28 | Ab Astra | New compounds |
| SE504459C2 (sv) * | 1994-07-15 | 1997-02-17 | Astra Ab | Förfarande för framställning av substituerade sulfoxider |
| GB9423968D0 (en) * | 1994-11-28 | 1995-01-11 | Astra Ab | Resolution |
| GB9423970D0 (en) * | 1994-11-28 | 1995-01-11 | Astra Ab | Oxidation |
-
1994
- 1994-07-15 SE SE9402510A patent/SE504459C2/sv not_active IP Right Cessation
-
1995
- 1995-07-03 EE EE9700006A patent/EE03354B1/xx unknown
- 1995-07-03 EP EP95926068A patent/EP0773940B2/en not_active Expired - Lifetime
- 1995-07-03 AT AT95926068T patent/ATE242233T1/de active
- 1995-07-03 DE DE69530987T patent/DE69530987T3/de not_active Expired - Lifetime
- 1995-07-03 RU RU97102162/04A patent/RU2157806C2/ru active
- 1995-07-03 DK DK95926068.8T patent/DK0773940T4/da active
- 1995-07-03 MX MX9700358D patent/MX9700358A/es unknown
- 1995-07-03 CA CA002193994A patent/CA2193994C/en not_active Expired - Lifetime
- 1995-07-03 JP JP50493896A patent/JP3795917B2/ja not_active Expired - Fee Related
- 1995-07-03 SI SI9530676T patent/SI0773940T2/sl unknown
- 1995-07-03 PT PT95926068T patent/PT773940E/pt unknown
- 1995-07-03 UA UA97020638A patent/UA47409C2/uk unknown
- 1995-07-03 WO PCT/SE1995/000818 patent/WO1996002535A1/en not_active Ceased
- 1995-07-03 US US08/492,087 patent/US5948789A/en not_active Expired - Lifetime
- 1995-07-03 ES ES95926068T patent/ES2199998T5/es not_active Expired - Lifetime
- 1995-07-03 KR KR1019970700221A patent/KR100356252B1/ko not_active Expired - Lifetime
- 1995-07-03 SK SK48-97A patent/SK284059B6/sk not_active IP Right Cessation
- 1995-07-03 AU AU29948/95A patent/AU688074B2/en not_active Expired
- 1995-07-03 BR BR9508292A patent/BR9508292A/pt not_active Application Discontinuation
- 1995-07-04 TW TW084106875A patent/TW372971B/zh not_active IP Right Cessation
- 1995-07-05 NZ NZ289959A patent/NZ289959A/en not_active IP Right Cessation
- 1995-07-05 HU HU9700108A patent/HU226361B1/hu unknown
- 1995-07-05 PL PL95318165A patent/PL186342B1/pl unknown
- 1995-07-05 CZ CZ0006497A patent/CZ297987B6/cs not_active IP Right Cessation
- 1995-07-05 CN CN95194956.XA patent/CN1070489C/zh not_active Expired - Lifetime
- 1995-07-06 IL IL11447795A patent/IL114477A/en not_active IP Right Cessation
- 1995-07-10 ZA ZA955724A patent/ZA955724B/xx unknown
- 1995-07-10 MA MA23950A patent/MA23611A1/fr unknown
- 1995-07-11 DZ DZ950088A patent/DZ1911A1/fr active
- 1995-07-11 EG EG57195A patent/EG24534A/xx active
- 1995-07-12 HR HR950401A patent/HRP950401B1/xx not_active IP Right Cessation
- 1995-07-13 TN TNTNSN95081A patent/TNSN95081A1/fr unknown
- 1995-07-14 YU YU47695A patent/YU49475B/sh unknown
- 1995-07-14 MY MYPI95001998A patent/MY113180A/en unknown
- 1995-07-14 TR TR95/00861A patent/TR199500861A2/xx unknown
- 1995-10-07 SA SA95160294A patent/SA95160294B1/ar unknown
-
1996
- 1996-06-28 AR ARP960103398A patent/AR003443A1/es active IP Right Grant
- 1996-12-27 IS IS4406A patent/IS1772B/is unknown
-
1997
- 1997-01-10 FI FI970102A patent/FI117672B/fi not_active IP Right Cessation
- 1997-01-10 FI FI970102D patent/FI117830B/fi active
- 1997-01-14 NO NO19970153A patent/NO312101B1/no not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI117672B (fi) | Menetelmä substituoitujen sulfoksidien syntetisoimiseksi | |
| JPH11508590A (ja) | エナンチオマーが富化されたベンゾイミダゾール誘導体を光学的に精製する方法 | |
| KR20100014468A (ko) | 에소메프라졸 마그네슘 2수화물의 제조방법 | |
| EP2035410A1 (en) | A novel process for the preparation of esomeprazole and salts thereof | |
| EP1748998A1 (en) | A novel stereoselective synthesis of benzimidazole sulfoxides | |
| CA2553877C (en) | Compounds useful for the synthesis of s- and r-omeprazole and a process for their preparation | |
| CN114621188A (zh) | 一种泮托拉唑的制备方法 | |
| HK1008331B (en) | Process for synthesis of substituted sulphoxides | |
| MXPA98000160A (en) | A process for the optic purification of derivatives of benzimidazol enriquecidos enantiomericame | |
| HK1098474B (en) | New compounds useful for the synthesis of s-and r-omeprazole and a process for their preparation | |
| HK1010193B (en) | A process for the optical purification of enantiomerically enriched benzimidazole derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC | Transfer of assignment of patent |
Owner name: ASTRAZENECA AB Free format text: ASTRAZENECA AB |
|
| FG | Patent granted |
Ref document number: 117830 Country of ref document: FI Effective date: 20070315 |
|
| FG | Patent granted |
Ref document number: 117830 Country of ref document: FI |
|
| MA | Patent expired |