NO312101B1 - Fremgangsmåte for syntese av substituerte sulfoksider, og slike produktforbindelser - Google Patents
Fremgangsmåte for syntese av substituerte sulfoksider, og slike produktforbindelser Download PDFInfo
- Publication number
- NO312101B1 NO312101B1 NO19970153A NO970153A NO312101B1 NO 312101 B1 NO312101 B1 NO 312101B1 NO 19970153 A NO19970153 A NO 19970153A NO 970153 A NO970153 A NO 970153A NO 312101 B1 NO312101 B1 NO 312101B1
- Authority
- NO
- Norway
- Prior art keywords
- chiral
- alkyl
- hydrogen
- mmol
- alkoxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 87
- 150000003462 sulfoxides Chemical class 0.000 title claims description 73
- 150000001875 compounds Chemical class 0.000 title claims description 71
- 230000015572 biosynthetic process Effects 0.000 title claims description 12
- 238000003786 synthesis reaction Methods 0.000 title claims description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 84
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 62
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 60
- 238000007254 oxidation reaction Methods 0.000 claims description 51
- 230000003647 oxidation Effects 0.000 claims description 49
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 41
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 39
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 35
- 239000010936 titanium Substances 0.000 claims description 33
- 239000000047 product Substances 0.000 claims description 32
- 229910052719 titanium Inorganic materials 0.000 claims description 32
- 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 31
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 150000002431 hydrogen Chemical group 0.000 claims description 25
- 238000002360 preparation method Methods 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 23
- 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 22
- -1 sulfoxide compound Chemical class 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical group 0.000 claims description 20
- 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 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 15
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 12
- 239000012043 crude product Substances 0.000 claims description 10
- 238000002425 crystallisation Methods 0.000 claims description 10
- 230000008025 crystallization Effects 0.000 claims description 10
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 claims description 8
- 239000003446 ligand Substances 0.000 claims description 8
- 239000007800 oxidant agent Substances 0.000 claims description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- LCKIEQZJEYYRIY-UHFFFAOYSA-N Titanium ion Chemical compound [Ti+4] LCKIEQZJEYYRIY-UHFFFAOYSA-N 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 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
- 125000002071 phenylalkoxy group Chemical group 0.000 claims description 5
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 5
- 125000004950 trifluoroalkyl group Chemical group 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 150000002009 diols Chemical class 0.000 claims description 4
- YREYEVIYCVEVJK-UHFFFAOYSA-N rabeprazole Chemical compound COCCCOC1=CC=NC(CS(=O)C=2NC3=CC=CC=C3N=2)=C1C YREYEVIYCVEVJK-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 3
- 150000007530 organic bases Chemical class 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 2
- 150000004703 alkoxides Chemical class 0.000 claims description 2
- 159000000011 group IA salts Chemical class 0.000 claims description 2
- 235000002906 tartaric acid Nutrition 0.000 claims description 2
- 239000011975 tartaric acid Substances 0.000 claims description 2
- KKKDZZRICRFGSD-UHFFFAOYSA-N 1-benzylimidazole Chemical compound C1=CN=CN1CC1=CC=CC=C1 KKKDZZRICRFGSD-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 106
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 79
- 239000000243 solution Substances 0.000 description 63
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 54
- 230000003287 optical effect Effects 0.000 description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
- 238000011914 asymmetric synthesis Methods 0.000 description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 150000003457 sulfones Chemical class 0.000 description 23
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 21
- 230000014759 maintenance of location Effects 0.000 description 20
- 238000003756 stirring Methods 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 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 17
- 238000004458 analytical method Methods 0.000 description 17
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 15
- 235000011114 ammonium hydroxide Nutrition 0.000 description 15
- 238000006243 chemical reaction Methods 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
- 238000001704 evaporation Methods 0.000 description 13
- 230000008020 evaporation Effects 0.000 description 13
- 239000010410 layer Substances 0.000 description 13
- 239000002244 precipitate Substances 0.000 description 12
- 150000003568 thioethers Chemical class 0.000 description 12
- 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 11
- 239000003480 eluent Substances 0.000 description 11
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 11
- 239000000463 material Substances 0.000 description 10
- 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 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- 125000004434 sulfur atom Chemical group 0.000 description 9
- 238000010626 work up procedure Methods 0.000 description 9
- 238000000605 extraction Methods 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 229960000381 omeprazole Drugs 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- 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 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
- 238000003818 flash chromatography Methods 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- HVAJOLFRLWQQQL-UHFFFAOYSA-N 6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1h-benzimidazole;sodium Chemical compound [Na].N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C HVAJOLFRLWQQQL-UHFFFAOYSA-N 0.000 description 5
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 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 4
- 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 4
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 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
- 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 4
- 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 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
- 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 3
- 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 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-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
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 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 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 125000001174 sulfone group Chemical group 0.000 description 3
- 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
- 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 2
- 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 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000012064 sodium phosphate buffer Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- JXOSPTBRSOYXGC-UHFFFAOYSA-N 1-Chloro-4-iodobutane Chemical compound ClCCCCI JXOSPTBRSOYXGC-UHFFFAOYSA-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
- HFOVHZUQZANCPI-UHFFFAOYSA-N 1-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfanyl]benzimidazole Chemical compound COC1=C(C)C=NC(CSC=2N(C3=CC=CC=C3N=2)OC)=C1C HFOVHZUQZANCPI-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
- UCUIRNGEPTXZBS-UHFFFAOYSA-N 2-[(4-cyclopropyl-3-methoxypyridin-2-yl)methylsulfinyl]-6-fluoro-1h-benzimidazole Chemical compound COC1=C(CS(=O)C=2NC3=CC=C(F)C=C3N=2)N=CC=C1C1CC1 UCUIRNGEPTXZBS-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
- 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
- 102000057234 Acyl transferases Human genes 0.000 description 1
- 108700016155 Acyl transferases Proteins 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 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
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 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
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 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
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000003699 antiulcer agent Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000004296 chiral HPLC Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000027119 gastric acid secretion Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229960003174 lansoprazole Drugs 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 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
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 239000012074 organic phase Substances 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
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 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 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003335 steric effect Effects 0.000 description 1
- 239000000126 substance 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
- 239000002699 waste material Substances 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)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9402510A SE504459C2 (sv) | 1994-07-15 | 1994-07-15 | Förfarande för framställning av substituerade sulfoxider |
| PCT/SE1995/000818 WO1996002535A1 (fr) | 1994-07-15 | 1995-07-03 | Procede de synthese de sulfoxydes substitues |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO970153L NO970153L (no) | 1997-01-14 |
| NO970153D0 NO970153D0 (no) | 1997-01-14 |
| NO312101B1 true NO312101B1 (no) | 2002-03-18 |
Family
ID=20394753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19970153A NO312101B1 (no) | 1994-07-15 | 1997-01-14 | Fremgangsmåte for syntese av substituerte sulfoksider, og slike produktforbindelser |
Country Status (42)
| Country | Link |
|---|---|
| US (1) | US5948789A (fr) |
| EP (1) | EP0773940B2 (fr) |
| JP (1) | JP3795917B2 (fr) |
| KR (1) | KR100356252B1 (fr) |
| CN (1) | CN1070489C (fr) |
| AR (1) | AR003443A1 (fr) |
| AT (1) | ATE242233T1 (fr) |
| AU (1) | AU688074B2 (fr) |
| BR (1) | BR9508292A (fr) |
| CA (1) | CA2193994C (fr) |
| CZ (1) | CZ297987B6 (fr) |
| DE (1) | DE69530987T3 (fr) |
| DK (1) | DK0773940T4 (fr) |
| DZ (1) | DZ1911A1 (fr) |
| EE (1) | EE03354B1 (fr) |
| EG (1) | EG24534A (fr) |
| ES (1) | ES2199998T5 (fr) |
| FI (2) | FI117672B (fr) |
| HK (1) | HK1008331A1 (fr) |
| HR (1) | HRP950401B1 (fr) |
| HU (1) | HU226361B1 (fr) |
| IL (1) | IL114477A (fr) |
| IS (1) | IS1772B (fr) |
| MA (1) | MA23611A1 (fr) |
| MX (1) | MX9700358A (fr) |
| MY (1) | MY113180A (fr) |
| NO (1) | NO312101B1 (fr) |
| NZ (1) | NZ289959A (fr) |
| PL (1) | PL186342B1 (fr) |
| PT (1) | PT773940E (fr) |
| RU (1) | RU2157806C2 (fr) |
| SA (1) | SA95160294B1 (fr) |
| SE (1) | SE504459C2 (fr) |
| SI (1) | SI0773940T2 (fr) |
| SK (1) | SK284059B6 (fr) |
| TN (1) | TNSN95081A1 (fr) |
| TR (1) | TR199500861A2 (fr) |
| TW (1) | TW372971B (fr) |
| UA (1) | UA47409C2 (fr) |
| WO (1) | WO1996002535A1 (fr) |
| YU (1) | YU49475B (fr) |
| ZA (1) | ZA955724B (fr) |
Families Citing this family (153)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6875872B1 (en) | 1993-05-28 | 2005-04-05 | Astrazeneca | Compounds |
| 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 |
| US6489346B1 (en) | 1996-01-04 | 2002-12-03 | The Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and method of using same |
| US5840737A (en) | 1996-01-04 | 1998-11-24 | The Curators Of The University Of Missouri | Omeprazole solution and method for using same |
| US6645988B2 (en) * | 1996-01-04 | 2003-11-11 | 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 |
| 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 |
| BR9810508A (pt) | 1997-07-03 | 2000-09-05 | Du Pont Pharm Co | Composto, composição farmacêutica e método de tratamento de uma desordem |
| SE9704183D0 (sv) * | 1997-11-14 | 1997-11-14 | Astra Ab | New process |
| US6174548B1 (en) | 1998-08-28 | 2001-01-16 | Andrx Pharmaceuticals, Inc. | Omeprazole formulation |
| US6096340A (en) * | 1997-11-14 | 2000-08-01 | Andrx Pharmaceuticals, Inc. | Omeprazole formulation |
| EP1056456A4 (fr) * | 1998-01-30 | 2006-10-25 | Sepracor Inc | Compositions et procedes d'utilisation du r-lansoprazole |
| JP2002512263A (ja) * | 1998-04-30 | 2002-04-23 | セプラコール， インク． | Ｓ−レイブプラゾール組成物及び方法 |
| CA2330139A1 (fr) * | 1998-04-30 | 1999-11-04 | Sepracor Inc. | Compositions a base de r-rabeprazole et procedes |
| 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 |
| TWI275587B (en) | 1999-06-17 | 2007-03-11 | Takeda Chemical Industries Ltd | A crystal of (R)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole |
| DE60020967T2 (de) | 1999-06-30 | 2006-05-04 | Takeda Pharmaceutical Co. Ltd. | Kristalle von lansoprazole |
| WO2001014366A1 (fr) * | 1999-08-25 | 2001-03-01 | Takeda Chemical Industries, Ltd. | Procede de preparation de derives optiquement actifs de sulfoxyde |
| US6262086B1 (en) | 1999-08-26 | 2001-07-17 | Robert R. Whittle | 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 |
| 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 |
| US6780880B1 (en) | 1999-08-26 | 2004-08-24 | Robert R. Whittle | FT-Raman spectroscopic measurement |
| US6326384B1 (en) | 1999-08-26 | 2001-12-04 | Robert R. Whittle | Dry blend pharmaceutical unit dosage form |
| US6312712B1 (en) | 1999-08-26 | 2001-11-06 | Robert R. Whittle | Method of improving bioavailability |
| US6312723B1 (en) | 1999-08-26 | 2001-11-06 | Robert R. Whittle | Pharmaceutical unit dosage form |
| US6316020B1 (en) * | 1999-08-26 | 2001-11-13 | Robert R. Whittle | Pharmaceutical formulations |
| US6268385B1 (en) | 1999-08-26 | 2001-07-31 | Robert R. Whittle | Dry blend pharmaceutical formulations |
| AU2001252595A1 (en) * | 2000-04-28 | 2001-11-12 | Takeda Chemical Industries Ltd. | Process for producing optically active sulfoxide derivative |
| ES2511774T3 (es) | 2000-05-15 | 2014-10-23 | Takeda Pharmaceutical Company Limited | Formas cristalinas de (R)-lansoprazol |
| KR100869677B1 (ko) | 2000-05-15 | 2008-11-21 | 다케다 야쿠힌 고교 가부시키가이샤 | 결정의 제조방법 |
| CA2775616C (fr) * | 2000-08-04 | 2013-09-17 | Takeda Pharmaceutical Company Limited | Sels de benzimidazoles et leur application |
| US7285668B2 (en) * | 2000-12-01 | 2007-10-23 | Takeda Pharmaceutical Company Limited | Process for the crystallization of (R)- or (S)-lansoprazole |
| AU2002338655A1 (en) * | 2001-04-13 | 2002-10-28 | Aspinterm Llc | Methods of preparing sulfinamide and sulfoxides |
| GB2376231A (en) * | 2001-06-06 | 2002-12-11 | Cipla Ltd | Benzimidazole-cyclodextrin inclusion complex |
| MXPA04007169A (es) * | 2002-01-25 | 2004-10-29 | Santarus Inc | Suministro transmucosal de inhibidores de bomba de protones. |
| CA2474246C (fr) * | 2002-03-05 | 2010-06-29 | Astrazeneca Ab | Sels d'alkylammonium d'omeprazole et d'esomeprazole |
| WO2003089408A2 (fr) * | 2002-04-22 | 2003-10-30 | Sun Pharmaceutical Industries Limited | Pyridinylmethyl-sulphinyl-benzimidazole substitue optiquement actif et sels |
| WO2004002982A2 (fr) * | 2002-06-27 | 2004-01-08 | Dr. Reddy's Laboratories Limited | Procede de preparation de composes sulfoxyde optiquement purs ou optiquement enrichis, notamment de l'esomeprazole amorphe et ses sels |
| MY148805A (en) | 2002-10-16 | 2013-05-31 | Takeda Pharmaceutical | Controlled release preparation |
| AU2003273000A1 (en) * | 2002-10-16 | 2004-05-04 | Takeda Pharmaceutical Company Limited | Stable solid preparations |
| EA200500673A1 (ru) | 2002-10-22 | 2005-12-29 | Рэнбакси Лабораториз Лимитед | Аморфная форма соли эзомепразола, способ ее получения и фармацевтическая композиция на её основе |
| DE10254167A1 (de) | 2002-11-20 | 2004-06-09 | Icon Genetics Ag | Verfahren zur Kontrolle von zellulären Prozessen in Pflanzen |
| SI1575941T1 (sl) * | 2002-12-06 | 2012-08-31 | Nycomed Gmbh | Postopek za pripravo (S)-pantoprazola |
| US7452998B2 (en) * | 2002-12-06 | 2008-11-18 | Nycomed Gmbh | Process for preparing optically pure active compounds |
| FR2848555B1 (fr) | 2002-12-16 | 2006-07-28 | Negma Gild | Enantiomere(-)du tenatoprazole et son application en therapeutique |
| BR0317425A (pt) * | 2002-12-16 | 2005-11-16 | Ranbaxy Lab Ltd | Sal de rabeprazol, composição farmacêutica contendo o mesmo e processo para sua preparação |
| CA2510849A1 (fr) | 2002-12-19 | 2004-07-08 | Teva Pharmaceutical Industries Ltd | Etats solides de sodium de pantoprazole, leurs procedes de preparation et procedes de preparation d'hydrates de sodium de pantoprazole connus |
| EP1583507A2 (fr) * | 2003-01-07 | 2005-10-12 | Ranbaxy Laboratories Limited | Sels de magnesium de derives de l'imidazole |
| CA2517005A1 (fr) * | 2003-02-20 | 2004-09-02 | Santarus, Inc. | Liberation immediate d'un complexe antacide d'omeprazole presentant une nouvelle formulation pour une elimination rapide et prolongee d'acide gastrique |
| CN1777598A (zh) * | 2003-02-28 | 2006-05-24 | 兰贝克赛实验室有限公司 | S－奥美拉唑的多晶型物 |
| US20040235904A1 (en) * | 2003-03-12 | 2004-11-25 | Nina Finkelstein | Crystalline and amorphous solids of pantoprazole and processes for their preparation |
| EP1611901B1 (fr) * | 2003-03-13 | 2013-07-10 | Eisai R&D Management Co., Ltd. | Medicament destiné à prevenir ou à traiter les grincements de dents |
| 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. |
| CN1842525A (zh) * | 2003-05-05 | 2006-10-04 | 兰贝克赛实验室有限公司 | 苯并咪唑衍生物的钡盐 |
| MXPA05013316A (es) | 2003-06-10 | 2006-03-17 | Teva Pharma | Proceso para preparar bencimidazoles 2[-(piridinil)metil]sulfinil-sustituidos y derivados clorados novedosos de pantoprazol. |
| 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 |
| AU2003288703A1 (en) * | 2003-12-05 | 2005-06-24 | 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 |
| WO2005105786A1 (fr) | 2004-04-28 | 2005-11-10 | Hetero Drugs Limited | Methode servant a preparer des composes de pyridinylmethyl-1h-benzimidazole sous forme d'enantiomeres simples ou enrichis |
| 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 |
| DE602004025386D1 (de) * | 2004-05-28 | 2010-03-18 | Hetero Drugs Ltd | Neue stereoselektive synthese von benzimidazolsulfoxiden |
| WO2005118569A1 (fr) * | 2004-06-02 | 2005-12-15 | Altana Pharma Ag | Procede permettant la preparation de composes pyridin-2-yl-methyl-sulfinyl-1h-benzimidazol |
| CA2570916C (fr) | 2004-06-16 | 2013-06-11 | Tap Pharmaceutical Products, Inc. | Forme posologique d'ipp a doses multiples |
| WO2006001755A1 (fr) * | 2004-06-24 | 2006-01-05 | Astrazeneca Ab | Nouvelle forme modifiee de cristaux de sels d'esomeprazole sodium |
| WO2006001753A1 (fr) * | 2004-06-24 | 2006-01-05 | Astrazeneca Ab | Nouveau procede de preparation de modifications de cristal a utiliser dans la preparation de sel de sodium d'esomeprazole |
| FR2876101B1 (fr) * | 2004-10-05 | 2007-03-02 | Sidem Pharma Sa Sa | Procede de preparation enantioselective de derives de sulfoxydes |
| SI1802584T1 (sl) * | 2004-10-11 | 2010-01-29 | Ranbaxy Lab Ltd | Postopki za pripravo substituiranih sulfoksidov |
| US7592111B2 (en) * | 2004-11-05 | 2009-09-22 | Xerox Corporation | Imaging member |
| JP4837722B2 (ja) * | 2005-03-25 | 2011-12-14 | リブゾン ファーマシューティカル グループ インク． | 置換スルホキシド化合物、その調製方法、およびその使用方法 |
| 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 |
| EP1885711A1 (fr) * | 2005-05-06 | 2008-02-13 | Glenmark Pharmaceuticals Limited | Sel de strontium d'esomeprazole, procede de preparation de ce sel et compositions pharmaceutiques le contenant |
| EP1907375B1 (fr) * | 2005-06-08 | 2013-07-24 | LEK Pharmaceuticals d.d. | Solvate cristallin de sodium d'omeprazole |
| US20070043085A1 (en) * | 2005-08-19 | 2007-02-22 | Glenmark Pharmaceuticals Limited | Process for the preparation of amorphous form of neutral esomeprazole |
| AU2006323245B2 (en) | 2005-12-05 | 2011-03-03 | Astrazeneca Ab | New process for the preparation of esomeprazole non-salt form |
| EP1801110A1 (fr) | 2005-12-22 | 2007-06-27 | KRKA, tovarna zdravil, d.d., Novo mesto | Sel d'arginine d'ésoméprazole |
| 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 |
| US7799925B2 (en) | 2005-12-28 | 2010-09-21 | Unión Químico Farmacéutica, S.A. | Process for the preparation of the (S)-enantiomer of omeprazole |
| 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 |
| BRPI0621832A2 (pt) | 2006-07-05 | 2013-03-19 | Lupin Ltd | processo para a preparaÇço de enantiâmeros oticamente puros ou oticamente enriquecidos de compostos de sulfàxido |
| WO2008018091A1 (fr) * | 2006-08-08 | 2008-02-14 | Jubilant Organosys Limited | Procédé de production de composés de sulfoxyde |
| EP2065379A4 (fr) | 2006-10-13 | 2011-01-19 | Eisai R&D Man Co Ltd | Benzimidazole présentant une activité inhibitrice de la sécrétion d'acide gastrique |
| 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 (fr) | 2007-01-18 | 2008-07-23 | LEK Pharmaceuticals D.D. | Procédé pour l'élimination de solvant des sels d'oméprazole |
| CA2678702A1 (fr) | 2007-02-21 | 2008-08-28 | Cipla Limited | Procede pour la preparation de esomeprazole magnesium dihydrate |
| EP2152691B1 (fr) * | 2007-06-07 | 2011-11-23 | Aurobindo Pharma Limited | Procédé amélioré pour préparer un inhibiteur de la pompe à protons optiquement actif |
| 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 |
| US20100210848A1 (en) * | 2007-10-03 | 2010-08-19 | Ipca Laboratories Ltd. | Process for optically active sulfoxide compounds |
| US8106210B2 (en) | 2007-10-08 | 2012-01-31 | Hetero Drugs Limited | Polymorphs of esomeprazole salts |
| CN102014638A (zh) | 2007-10-12 | 2011-04-13 | 武田制药北美公司 | 与食物摄入无关的治疗胃肠病症的方法 |
| 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 (fr) * | 2008-05-27 | 2009-12-03 | Sk Chemicals Co., Ltd. | Procédé amélioré de préparation de (s)-oméprazole à partir d'un racémate d'oméprazole à l’aide d'un agent de résolution optique |
| EP2143722A1 (fr) | 2008-07-09 | 2010-01-13 | Lek Pharmaceuticals D.D. | Procédé de préparation de sodium ésoméprazole de haute pureté chimique et nouvelles formes de sodium ésoméprazole |
| WO2010039885A2 (fr) * | 2008-09-30 | 2010-04-08 | Teva Pharmaceutical Industries Ltd. | Formes cristallines du dexlansoprazole |
| EP2264024A1 (fr) | 2008-10-14 | 2010-12-22 | LEK Pharmaceuticals d.d. | Procédé de préparation d'inhibiteurs de la pompe à protons énantiomériquement enrichis |
| 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 (fr) | 2009-02-24 | 2010-09-02 | Cipla Limited | Polymorphe de l'ésoméprazole de potassium et sa préparation |
| 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 |
| EP2438057A4 (fr) * | 2009-06-02 | 2013-12-25 | Sun Pharmaceutical Ind Ltd | Procédé d'élaboration de composés sulfoxyde |
| IT1395118B1 (it) | 2009-07-29 | 2012-09-05 | Dipharma Francis Srl | Procedimento per la preparazione di dexlansoprazolo cristallino |
| US8748619B2 (en) | 2009-11-12 | 2014-06-10 | Hetero Research Foundation | Process for the resolution of omeprazole |
| US20130197232A1 (en) | 2010-01-29 | 2013-08-01 | Ranbaxy Laboratories Limited | Process for the preparation of crystalline forms of dexlansoprazole |
| AU2011268774A1 (en) | 2010-06-24 | 2013-01-17 | 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 (fr) | 2012-03-22 | 2013-09-26 | Cipla Limited | Formes solvatées de glycérol de (r)-2-[[[3-methyl-4(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl]sulphinyl]-lh-benzimidazole |
| 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 |
| EP2929885A1 (fr) | 2014-04-11 | 2015-10-14 | Sanovel Ilac Sanayi ve Ticaret A.S. | Combinaisons pharmaceutiques de rivaroxaban et d'inhibiteurs de la pompe à protons |
| EP2980086B1 (fr) | 2014-07-29 | 2016-06-15 | F.I.S.- Fabbrica Italiana Sintetici S.p.A. | Procédé efficace pour la préparation d'ésoméprazole (S)-binol complexe |
| EP3239146A4 (fr) | 2014-12-26 | 2018-05-30 | The University of Tokyo | Procédé de fabrication d'un composé inhibiteur de la pompe à protons ayant une activité optique |
| 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 |
| ES2615637T3 (es) | 2015-03-06 | 2017-06-07 | F.I.S.- Fabbrica Italiana Sintetici S.P.A. | Procedimiento mejorado para la purificación óptica del esomeprazol |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| CN113845510A (zh) * | 2020-06-27 | 2021-12-28 | 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 (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE7804231L (sv) * | 1978-04-14 | 1979-10-15 | Haessle Ab | Magsyrasekretionsmedel |
| GB2189698A (en) * | 1986-04-30 | 1987-11-04 | Haessle Ab | Coated omeprazole tablets |
| DE4035455A1 (de) * | 1990-11-08 | 1992-05-14 | Byk Gulden Lomberg Chem Fab | Enantiomerentrennung |
| 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 |
| GB9423970D0 (en) * | 1994-11-28 | 1995-01-11 | Astra Ab | Oxidation |
| GB9423968D0 (en) * | 1994-11-28 | 1995-01-11 | Astra Ab | Resolution |
-
1994
- 1994-07-15 SE SE9402510A patent/SE504459C2/sv not_active IP Right Cessation
-
1995
- 1995-07-03 BR BR9508292A patent/BR9508292A/pt not_active Application Discontinuation
- 1995-07-03 US US08/492,087 patent/US5948789A/en not_active Expired - Lifetime
- 1995-07-03 JP JP50493896A patent/JP3795917B2/ja not_active Expired - Fee Related
- 1995-07-03 RU RU97102162/04A patent/RU2157806C2/ru active
- 1995-07-03 DK DK95926068.8T patent/DK0773940T4/da active
- 1995-07-03 PT PT95926068T patent/PT773940E/pt unknown
- 1995-07-03 KR KR1019970700221A patent/KR100356252B1/ko not_active IP Right Cessation
- 1995-07-03 AT AT95926068T patent/ATE242233T1/de active
- 1995-07-03 WO PCT/SE1995/000818 patent/WO1996002535A1/fr active Search and Examination
- 1995-07-03 AU AU29948/95A patent/AU688074B2/en not_active Expired
- 1995-07-03 SK SK48-97A patent/SK284059B6/sk not_active IP Right Cessation
- 1995-07-03 UA UA97020638A patent/UA47409C2/uk unknown
- 1995-07-03 DE DE69530987T patent/DE69530987T3/de not_active Expired - Lifetime
- 1995-07-03 MX MX9700358D patent/MX9700358A/es unknown
- 1995-07-03 EE EE9700006A patent/EE03354B1/xx unknown
- 1995-07-03 ES ES95926068T patent/ES2199998T5/es not_active Expired - Lifetime
- 1995-07-03 CA CA002193994A patent/CA2193994C/fr not_active Expired - Lifetime
- 1995-07-03 EP EP95926068A patent/EP0773940B2/fr not_active Expired - Lifetime
- 1995-07-03 SI SI9530676T patent/SI0773940T2/sl unknown
- 1995-07-04 TW TW084106875A patent/TW372971B/zh not_active IP Right Cessation
- 1995-07-05 HU HU9700108A patent/HU226361B1/hu unknown
- 1995-07-05 CZ CZ0006497A patent/CZ297987B6/cs not_active IP Right Cessation
- 1995-07-05 CN CN95194956A patent/CN1070489C/zh not_active Expired - Lifetime
- 1995-07-05 NZ NZ289959A patent/NZ289959A/en not_active IP Right Cessation
- 1995-07-05 PL PL95318165A patent/PL186342B1/pl unknown
- 1995-07-06 IL IL11447795A patent/IL114477A/en not_active IP Right Cessation
- 1995-07-10 MA MA23950A patent/MA23611A1/fr unknown
- 1995-07-10 ZA ZA955724A patent/ZA955724B/xx unknown
- 1995-07-11 EG EG57195A patent/EG24534A/xx active
- 1995-07-11 DZ DZ950088A patent/DZ1911A1/fr 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
-
1998
- 1998-07-17 HK HK98109230A patent/HK1008331A1/xx not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO312101B1 (no) | Fremgangsmåte for syntese av substituerte sulfoksider, og slike produktforbindelser | |
| EP0836601B1 (fr) | Procede de purification optique pour derives de benzimidazole enrichis par enantiomorphe | |
| US20050288334A1 (en) | Process for preparing optically pure active compounds | |
| CA2553877C (fr) | Compose utile pour la synthese de s- et r-omeprazole et procede de preparation associe | |
| MXPA98000160A (en) | A process for the optic purification of derivatives of benzimidazol enriquecidos enantiomericame |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1K | Patent expired |