FI117672B - Menetelmä substituoitujen sulfoksidien syntetisoimiseksi - Google Patents

Menetelmä substituoitujen sulfoksidien syntetisoimiseksi Download PDF

Info

Publication number: FI117672B
Authority: FI; Finland
Prior art keywords: alkyl; eller; alkoxy; chiral; halogen
Prior art date: 1994-07-15

Application number

FI970102A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI970102L (fi

FI970102A0 (fi

Inventor

Erik Magnus Larsson

Urban Jan Stenhede

Henrik Soerensen

Unge Per Oskar Sverker Von

Hanna Kristina Cotton

Original Assignee

Astrazeneca Ab

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1994-07-15

Filing date

1997-01-10

Publication date

2007-01-15

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=20394753&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=FI117672(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1997-01-10 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

1997-01-10 Publication of FI970102L publication Critical patent/FI970102L/fi

1997-01-10 Publication of FI970102A0 publication Critical patent/FI970102A0/fi

2007-01-15 Application granted granted Critical

2007-01-15 Publication of FI117672B publication Critical patent/FI117672B/fi

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)

FI970102A 1994-07-15 1997-01-10 Menetelmä substituoitujen sulfoksidien syntetisoimiseksi FI117672B (fi)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
SE9402510		1994-07-15
SE9402510A SE504459C2 (sv)	1994-07-15	1994-07-15	Förfarande för framställning av substituerade sulfoxider
SE9500818		1995-07-03
PCT/SE1995/000818 WO1996002535A1 (fr)	1994-07-15	1995-07-03	Procede de synthese de sulfoxydes substitues

Publications (3)

Publication Number	Publication Date
FI970102L FI970102L (fi)	1997-01-10
FI970102A0 FI970102A0 (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 (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)
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)

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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
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
US5840737A (en)	1996-01-04	1998-11-24	The Curators Of The University Of Missouri	Omeprazole solution and method for using same
US6489346B1 (en) *	1996-01-04	2002-12-03	The Curators Of The University Of Missouri	Substituted benzimidazole dosage forms and method of using same
US6747155B2 (en)	1997-05-30	2004-06-08	Astrazeneca Ab	Process
SE510650C2 (sv)	1997-05-30	1999-06-14	Astra Ab	Ny förening
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
US6096340A (en)	1997-11-14	2000-08-01	Andrx Pharmaceuticals, Inc.	Omeprazole formulation
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
WO1999038513A1 (fr) *	1998-01-30	1999-08-05	Sepracor Inc.	Compositions et procedes d'utilisation du r-lansoprazole
CA2330324A1 (fr) *	1998-04-30	1999-11-04	Sepracor Inc.	Compositions a base de s-rabeprazole et procedes
AU3870599A (en) *	1998-04-30	1999-11-16	Sepracor, Inc.	R-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
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
ATE298334T1 (de)	1999-06-30	2005-07-15	Takeda Pharmaceutical	Kristalle von lansoprazole
AU6727700A (en) *	1999-08-25	2001-03-19	Takeda Chemical Industries Ltd.	Process for the preparation of optically active sulfoxide derivatives
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
US6780880B1 (en)	1999-08-26	2004-08-24	Robert R. Whittle	FT-Raman spectroscopic measurement
US6316020B1 (en) *	1999-08-26	2001-11-13	Robert R. Whittle	Pharmaceutical formulations
US6312723B1 (en)	1999-08-26	2001-11-06	Robert R. Whittle	Pharmaceutical unit dosage form
US6262086B1 (en)	1999-08-26	2001-07-17	Robert R. Whittle	Pharmaceutical unit dosage form
US6268385B1 (en)	1999-08-26	2001-07-31	Robert R. Whittle	Dry blend pharmaceutical formulations
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
US6312712B1 (en)	1999-08-26	2001-11-06	Robert R. Whittle	Method of improving bioavailability
US6326384B1 (en)	1999-08-26	2001-12-04	Robert R. Whittle	Dry blend pharmaceutical unit dosage form
WO2001083473A1 (fr) *	2000-04-28	2001-11-08	Takeda Chemical Industries, Ltd.	Procede de production d'un derive de sulfoxide optiquement actif
KR100869677B1 (ko)	2000-05-15	2008-11-21	다케다 야쿠힌 고교 가부시키가이샤	결정의 제조방법
DE60131649T2 (de)	2000-05-15	2008-10-30	Takeda Pharmaceutical Co. Ltd.	Verfahren zur herstellung eines kristalls
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
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- 1995-07-03 US US08/492,087 patent/US5948789A/en not_active Expired - Lifetime
- 1995-07-03 CA CA002193994A patent/CA2193994C/fr not_active Expired - Lifetime
- 1995-07-03 DK DK95926068.8T patent/DK0773940T4/da active
- 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
- 1995-07-04 TW TW084106875A patent/TW372971B/zh not_active IP Right Cessation
- 1995-07-05 CN CN95194956.XA 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
- 1995-07-05 CZ CZ0006497A patent/CZ297987B6/cs not_active IP Right Cessation
- 1995-07-05 HU HU9700108A patent/HU226361B1/hu unknown
- 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 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 TR TR95/00861A patent/TR199500861A2/xx unknown
- 1995-07-14 MY MYPI95001998A patent/MY113180A/en unknown
- 1995-07-14 YU YU47695A patent/YU49475B/sh 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

Publication number	Publication date
IL114477A0 (en)	1995-11-27
SA95160294B1 (ar)	2006-07-31
NO312101B1 (no)	2002-03-18
ATE242233T1 (de)	2003-06-15
KR970704731A (ko)	1997-09-06
CA2193994C (fr)	2005-05-03
JPH10504290A (ja)	1998-04-28
EP0773940B2 (fr)	2010-11-17
UA47409C2 (uk)	2002-07-15
SI0773940T1 (en)	2004-02-29
IS1772B (is)	2001-06-01
EP0773940A1 (fr)	1997-05-21
AU688074B2 (en)	1998-03-05
AR003443A1 (es)	1998-08-05
MA23611A1 (fr)	1996-04-01
SK284059B6 (sk)	2004-09-08
CA2193994A1 (fr)	1996-02-01
WO1996002535A1 (fr)	1996-02-01
TR199500861A2 (tr)	1996-06-21
MX9700358A (es)	1997-04-30
SK4897A3 (en)	1997-08-06
CZ297987B6 (cs)	2007-05-16
SE504459C2 (sv)	1997-02-17
DE69530987D1 (de)	2003-07-10
CZ6497A3 (en)	1997-06-11
CN1157614A (zh)	1997-08-20
NO970153L (no)	1997-01-14
FI970102L (fi)	1997-01-10
DZ1911A1 (fr)	2002-02-17
EG24534A (en)	2009-08-30
DK0773940T3 (da)	2003-09-15
DE69530987T2 (de)	2004-05-19
JP3795917B2 (ja)	2006-07-12
DK0773940T4 (da)	2011-02-07
IS4406A (is)	1996-12-27
SI0773940T2 (sl)	2011-02-28
EP0773940B1 (fr)	2003-06-04
KR100356252B1 (ko)	2002-11-18
FI117830B (fi)	2007-03-15
YU49475B (sh)	2006-05-25
BR9508292A (pt)	1997-12-23
YU47695A (sh)	1998-07-10
PL318165A1 (en)	1997-05-26
HK1008331A1 (en)	1999-05-07
ZA955724B (en)	1996-01-15
FI970102A0 (fi)	1997-01-10
SE9402510D0 (sv)	1994-07-15
NZ289959A (en)	1998-01-26
US5948789A (en)	1999-09-07
ES2199998T5 (es)	2011-03-16
HUT76642A (en)	1997-10-28
PT773940E (pt)	2003-10-31
SE9402510L (sv)	1996-01-16
IL114477A (en)	2001-07-24
MY113180A (en)	2001-12-31
AU2994895A (en)	1996-02-16
DE69530987T3 (de)	2011-07-07
HRP950401B1 (en)	2004-04-30
RU2157806C2 (ru)	2000-10-20
TW372971B (en)	1999-11-01
PL186342B1 (pl)	2003-12-31
HRP950401A2 (en)	1997-10-31
TNSN95081A1 (fr)	1996-02-06
EE03354B1 (et)	2001-02-15
CN1070489C (zh)	2001-09-05
NO970153D0 (no)	1997-01-14
HU226361B1 (en)	2008-09-29
WO1996002535A8 (fr)	1999-12-23
ES2199998T3 (es)	2004-03-01

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